Organometallics
Article
1
fitted with a reflux condenser. The resulting reaction mixture was
heated to 62 °C in an open atmosphere for 8 h.
N-(1,3-Thiazol-2-yl)benzamide (Entry 10). H NMR (CDCl 400
3,
MHz): 6.48 (br, 1H), 6.86−6.89 (m, 1H), 7.07−7.09 (m, 1H), 7.10−
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Recycling of catalyst. After completion of the reaction of each
cycle, the product mixture was cooled to room temperature; the
catalyst was recovered by centrifugation and then washed thoroughly
with diethyl ether and finally with hexane. The recovered catalyst was
dried under vacuum at 100−120 °C overnight. This used catalyst was
re-employed in five successive cycles under identical conditions. The
combined organic layers were concentrated in vacuo, and the
remaining residue was purified by column chromatography (n-
hexane/EtOAc: 200/1) to yield a compound.
7.19 (m, 2H), 7.21−7.38 (m, 3H) ppm. C{ H}NMR (CDCl 100
3
,
MHz): 126.9,127.9, 128.6, 130.8, 138.3, 143.1, 166.0, 172.5 ppm.
Assignment of signals was confirmed by DEPT-135 NMR studies.
Phenyl(piperidin-1-yl)methanone (Entry 11, CAS No.: 776-75-0).
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H NMR (CDCl 400 MHz): 1.52 (bs, 2H), 1.67 (bs, 4H), 3.34 (bs,
3,
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1
2H), 3.72 (bs, 2H), 7.39 (s, 5H) ppm. C{ H}NMR (CDCl 100
3
,
MHz): 24.5, 25.6, 26.5, 43.3, 48.8, 126.8, 128.3, 129.5, 136.2, 170.6
ppm. Assignment of signals was confirmed by DEPT-135 NMR
studies.
1
Spectral Data for the Amide Compounds. N-Benzylbenza-
Phenyl(pyrrolidin-1-yl)methanone (Entry 12). H NMR (CDCl
3
,
1
mide (Entry 1, CAS No.: 1485-70-7). H NMR (CDCl 400 MHz):
3
,
400 MHz): 1.84−1.95 (m, 4H), 3.41(t, J = 6.8 Hz, 2H), 3.64 (t, J = 6.8
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4
7
(
.65(d, J = 5.6 Hz, CH2, 2H), 6.43 (bs, 1H), 7.25−7.36 (m, 1H),
Hz, 2H), 7.38−7.39 (m, 3H), 7.49−7.51(m, 2H) ppm. C{ H}NMR
.40−7.44 (m, 4H), 7.47−7.49(m, 2H), 7.51 (t, J = 3.6 Hz, 1H), 7.78
(CDCl 100 MHz): 24.4, 26.4, 46.2,49.6, 127.1, 128.2, 129.8, 137.2,
3,
q, J = 3.6 Hz, 2H) ppm. 13C{ H}NMR (CDCl 100 MHz): 44.2,
1
3,
169.8 ppm. Assignment of signals was confirmed by DEPT-135 NMR
studies. Spectral data are consistent with literature values.
Morpholin-4-ylphenyl-methanone (Entry 13). H NMR (CDCl
400 MHz): 3.29−3.32 (m, 2H), 3.46 (t, J = 6.8 Hz, 2H), 3.78 (t, J =
6.8 Hz, 4H),7.41 (s, 5H) ppm. C{ H}NMR (CDCl 100 MHz):
43.0, 48.4, 66.9, 127.1, 128.5, 129.9, 135.3, 171.1 ppm. Assignment of
signals was confirmed by DEPT-135 NMR studies. Spectral data are
consistent with literature values.
Imidazol-1-yl-phenyl-methanone (Entry 14). H NMR (CDCl
400 MHz): 7.46−7.50 (m, 3H), 7.59−7.63 (m, 2H), 8.11−8.13 (m,
3H) ppm. C{ H}NMR (CDCl 100 MHz): 116.4, 120.0, 128.5,
3,
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127.0, 127.7, 127.9, 128.6, 128.8, 131.6, 134.4, 138.2, 167.4(NCO)
1
ppm. Assignment of signals was confirmed by DEPT-135 NMR
studies.
3,
N-(4-Nitrophenyl)benzamide (Entry 2). 1H NMR (CDCl3, 400
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1
3,
MHz): 7.51−7.63 (m, 3H), 7.85−7.89 (m, 4H), 8.22 (bs, 1H), 8.27
1
(
d, J = 9 Hz, 2H) ppm. 13C{ H}NMR (CDCl 100 MHz): 117.8,
3,
3
8
1
21.0, 128.5, 129.3, 130.2, 133.8, 143.1, 166.3 ppm. Assignment of
1
signals was confirmed by DEPT-135 NMR studies. Spectral data are
consistent with literature values.
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,
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1
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N-(4-Bromophenyl)benzamide (Entry 3, CAS No.: 7702-38-7). H
NMR (CDCl 400 MHz): 7.48−7.57 (m, 7H), 7.80 (bs, 1H), 7.81−
130.2, 133.6, 141.5, 171.3 ppm. Assignment of signals was confirmed
by DEPT-135 NMR studies.
3
,
13
1
7
1
.87 (m, 2H) ppm. C{ H}NMR (CDCl 100 MHz): 122.3, 127.0,
3,
Benzoimidazol-1-yl-phenyl-methanone (Entry 15). 1H NMR
(CDCl3, 400 MHz): 7.22−7.24 (m, 2H), 7.42 (t, J = 7.6, 2H),
27.7, 128.7, 129.0, 131.3, 139.9,165.3 ppm. Assignment of signals was
confirmed by DEPT-135 NMR studies. Spectral data are consistent
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1
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with literature values.
N-(4-Methoxyphenyl)benzamide (Entry 4). H NMR (CDCl 400
7.53−7.61 (m, 2H), 8.12−8.22 (m, 3H), 8.72 (s, 1H) ppm. C{ H}-
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3,
NMR (CDCl 100 MHz): 116.4, 119.5, 120.8, 127.0, 128.5, 130.2,
3,
MHz): 3.74 (s, 3H), 6.74 (d, J = 8.8 Hz, 2H), 7.45−7.54 (m, 5H), 7.80
133.6, 141.5, 172.5 ppm. Assignment of signals was confirmed by
DEPT-135 NMR studies. Spectral data are consistent with literature
values.
N-Cyclohexylbenzamide (Entry 16). H NMR (CDCl 400 MHz):
1
(
bs, 1H), 7.86 (d, J = 7.2 Hz, 2H) ppm. 13C{ H}NMR (CDCl 100
3,
3
9
MHz): 56.0, 114.4, 128.3, 129.6, 130.5, 132.8, 155.0, 166.7 ppm.
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Assignment of signals was confirmed by DEPT-135 NMR studies.
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,
3
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Spectral data are consistent with literature values.
1.28−1.38 (m, 5H), 1.56−1.82 (m, 5H), 4.13 (d, J = 7.2 Hz, 1H), 6.48
1
13
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N-(4-Ethoxyphenyl)benzamide (Entry 5). H NMR (CDCl 400
(bs, 1H), 7.35−7.68 (m, 5H) ppm. C{ H}NMR (CDCl 100 MHz):
3,
3,
MHz): 1.41(t, J = 6.8 Hz, 3H), 4.03(q, J = 7.2 Hz, 2H), 6.90 (d, J = 8.8
Hz, 2H), 7.46−7.54 (m, 5H), 7.74 (bs,1H), 7.86 (d, J = 7.2 Hz, 2H)
ppm. 13C{ H}NMR (CDCl 100 MHz): 14.9, 63.8, 114.9, 122.0,
24.9, 25.3, 33.5, 45.4, 128.4, 130.1, 133.7, 167.8 ppm. Assignment of
signals was confirmed by DEPT-135 NMR studies. Spectral data are
1
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3,
consistent with literature values.
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127.0, 128.8, 130.9, 131.7, 135.0, 156.0, 165.6 ppm. Assignment of
N,N′-Benzene-1,4-diyldibenzamide (Entry 17). H NMR (CDCl
3
,
signals was confirmed by DEPT-135 NMR studies. Spectral data are
400 MHz): 6.77 (bs, 2H), 7.48 (t, J = 7.6 Hz, 7H), 7.60 (d, J = 7.2 Hz,
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13
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consistent with literature values.
N-Benzylpyridine-2-carboxamide (Entry 6). H NMR (CDCl 400
3H), 8.12(d, J = 7.6 Hz, 4H) ppm. C{ H}NMR (CDCl 100 MHz):
3,
1
3,
117.1, 121.0, 128.5, 130.2, 133.8, 144.0, 166.0 ppm. Assignment of
signals was confirmed by DEPT-135 NMR studies.1
MHz): 4.80 (d, J = 8.4 Hz, 2H), 7.17−7.37 (m, 6H), 7.32 (s, 2H), 7.58
(
d, J = 7.6 Hz, 1H),7.65−7.69 (m, 1H), 8.38 (bs, 1H), 8.46 (d, J = 4.4
N,N′-Pyridine-2,6-diyldibenzamide (Entry 18). H NMR (CDCl
3
,
13
1
Hz, 1H) ppm. C{ H}NMR (CDCl 100 MHz): 42.1, 121.3, 124.8,
400 MHz): 7.41−7.48 (m, 6H), 7.53 (d, J = 8 Hz, 1H), 7.60 (t, J = 7.6
Hz, 1H), 8.04 (t, J = 7.6 Hz, 2H), 8.11 (d, J = 7.6 Hz, 3H), 8.31 (bs,
3,
1
26.8, 127.1, 128.5, 138.7, 142.6, 148.8, 149.3, 166.7 ppm. Assignment
2H) ppm. 13C{ H}NMR (CDCl3 100 MHz): 112.8, 128.3, 129.5,
1
of signals was confirmed by DEPT-135 NMR studies. Spectral data are
consistent with literature values.
N-Benzylthiophene-2-carboxamide (Entry 7). H NMR (CDCl
,
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130.2, 132.8, 133.7, 155.9, 166.7 ppm. Assignment of signals was
confirmed by DEPT-135 NMR studies. Spectral data are consistent
1
3,
4
0
4
00 MHz): 4.42 (d, J = 6 Hz, 2H), 6.50 (bs, 1H), 7.15−7.21 (m, 1H),
with literature values.
N-[(1S)-1-Phenylethyl]benzamide (Entry 19). H NMR (CDCl
400 MHz): 1.59 (d, J = 7.2 Hz, 3H), 5.3 (t, J = 7.2 Hz, 1H), 6.57 (bs,
1H), 7.24−7.28 (m, 1H), 7.32−7.39 (m, 6H), 7.41−7.49 (m, 1H),
7.76 (t, J = 7.2 Hz, 2H) ppm. 13C{ H}NMR (CDCl 100 MHz): 21.0,
49.2, 126.3, 127.0, 127.4, 128.5, 131.5, 134.6, 143.2, 166.7 ppm.
Assignment of signals was confirmed by DEPT-135 NMR studies.
(2S)-(Benzoylamino)(phenyl)ethanoic Acid (Entry 20). H NMR
1
7.24−7.28 (m, 5H,), 7.35 (d, J = 4 Hz, 1H), 7.37 (d, J = 4.4 Hz, 1H)
3
,
13
1
ppm. C{ H}NMR (CDCl 100 MHz): 45.4, 127.2, 127.7, 128.6,
3,
128.9, 129.3, 130.3, 134.3, 136.4, 162.1 ppm. Assignment of signals
1
was confirmed by DEPT-135 NMR studies. Spectral data are
3,
33
consistent with literature values.
N-Benzyl-1H-pyrrole-2-carboxamide (Entry 8). H NMR (CDCl
1
3,
1
4
8
00 MHz): 4.70 (d, J = 4 Hz, 2H), 6.48 (bs, 1H), 7.06−7.23 (m, 3H),
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1
.21−8.28 (m, 5H), 9.92 (bs, 1H) ppm. C{ H}NMR (CDCl 100
(CDCl 400 MHz): 5.81(d, 6.8 Hz, 1H), 7.45−7.59 (m, 8H), 7.81 (d,
3,
3,
13
1
MHz): 45.9, 107.6, 117.1, 128.3, 129.8, 132.6, 136.9, 143.1, 159.8 ppm.
7.2 Hz, 2H), 8.11 (d, 7.6 Hz, 1H) ppm. C{ H}NMR (CDCl 100
3,
Assignment of signals was confirmed by DEPT-135 NMR studies.
MHz): 57.1, 114.1, 127.4, 128.4, 128.7, 130.1, 132.2, 133.2, 139.3,
1
N-Benzyl-1H-indole-3-carboxamide (Entry 9). H NMR (CDCl
167.0, 172.2 ppm. Assignment of signals was confirmed by DEPT-135
3,
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4
6
00 MHz): 4.48 (d, J = 5.6 Hz, 2H), 6.35 (bs, 1H), 7.10−7.24 (m,
NMR studies. Spectral data are consistent with literature values.
H), 7.47(d, J = 7.6 Hz, 1H), 7.97 (d, J = 2.4 Hz, 1H), 8.37 (d, J = 7.6
X-ray Structure Determinations. Crystals 5−8 suitable for
single- crystal X-ray diffraction were obtained from vapor diffusion of
dichloromethane into an ethanol solution at room temperature. A
single crystal of suitable size was covered with Paratone oil, mounted
on the top of a glass fiber, and transferred to a Bruker SMART APEX
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Hz, 1H), 8.81(d, J = 8 Hz, 1H), 11.7 (s, 1H) ppm. C{ H}NMR
CDCl3, 100 MHz): 45.0, 102.6, 114.1, 127.0, 127.2, 128.0, 128.3,
28.5, 128.6, 130.8, 136.1, 139.3, 162.1 ppm. Assignment of signals
was confirmed by DEPT-135 NMR studies.
(
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dx.doi.org/10.1021/om500556b | Organometallics 2014, 33, 4269−4278