F
G. Toyooka et al.
Paper
Synthesis
13C NMR (101 MHz, CDCl3): δ = 60.0 [s, CN(CH3)2], 45.5 [s, N(CH3)2],
31.9 (s, CH2), 29.6 (s, CH2), 29.3 (s, CH2), 27.9 (s, CH2), 27.5 (s, CH2),
22.7 (s, CH2), 14.1 (s, CH3).
13C NMR (101 MHz, CDCl3): δ = 136.4 (s, Carom), 134.3 (s, Carom), 130.9
(s, Carom), 129.4 (s, Carom), 128.2 (s, Carom), 126.6 (s, Carom), 60.8 (s, CH2),
45.1 [s, N(CH3)2].
N,N-Dimethyloctan-2-amine (Table 2, entry 7)19
N,N-Dimethyl(3-chlorophenyl)methanamine (Table 2, entry 14)20
Yellow oil; yield: 150.5 mg (0.957 mmol, 95%); eluent: EtOAc/Et2NH
(50:1).
Yellow oil; yield: 158.6 mg (0.935 mmol, 93%); eluent: hexane/EtOAc/
Et2NH (95:5:2).
1H NMR (400 MHz, CDCl3): δ = 2.50–2.42 (m, 1 H, CH), 2.22 [s, 6 H,
N(CH3)2], 1.51–1.18 (m, 10 H, CH2), 0.93 (d, J = 7 Hz, 3 H, CH3), 0.88 (t,
J = 7 Hz, 3 H, CH3).
13C NMR (101 MHz, CDCl3): δ = 59.2 [s, CN(CH3)2], 40.6 [s, N(CH3)2],
33.6 (s, CH2), 31.9 (s, CH2), 29.7 (s, CH2), 26.8 (s, CH2), 22.7 (s, CH2),
14.1 (s, CH3), 13.6 (s, CH3).
1H NMR (400 MHz, CDCl3): δ = 7.21–7.11 (m, 4 Harom), 3.33 (s, 2 H,
CH2), 2.18 [s, 6 H, N(CH3)2].
13C NMR (101 MHz, CDCl3): δ = 141.2 (s, Carom), 134.2 (s, Carom), 129.5
(s, Carom), 129.0 (s, Carom), 127.2 (s, Carom), 127.1 (s, Carom), 63.8 (s, CH2),
45.4 [s, N(CH3)2].
N,N-Dimethyl(4-chlorophenyl)methanamine (Table 2, entry 15)20
N,N-Dimethyl(2-methylphenyl)methanamine (Table 2, entry 9)20
Yellow oil; yield: 166.9 mg (0.984 mmol, 98%); eluent: hexane/EtOAc/
Et2NH (95:5:2).
1H NMR (400 MHz, CDCl3): δ = 7.30–7.22 (m, 4 Harom), 3.38 (s, 2 H,
CH2), 2.22 [s, 6 H, N(CH3)2].
13C NMR (101 MHz, CDCl3): δ = 137.5 (s, Carom), 132.7 (s, Carom), 130.3
Yellow oil; yield: 131.8 mg (0.883 mmol, 88%); eluent: hexane/EtOAc/
Et2NH (95:5:2).
1H NMR (400 MHz, CDCl3): δ = 7.26–7.12 (m, 4 Harom), 3.37 (s, 2 H,
CH2), 2.36 (s, 3 H, ArCH3), 2.24 [s, 6 H, N(CH3)2].
13C NMR (101 MHz, CDCl3): δ = 137.3 (s, Carom), 137.2 (s, Carom), 130.3
(s, Carom), 129.9 (s, Carom), 127.1 (s, Carom), 125.6 (s, Carom), 62.1 (s, CH2),
45.6 [s, N(CH3)2], 19.2 (s, ArCH3).
(s, Carom), 128.4 (s, Carom), 63.6 (s, CH2), 45.3 [s, N(CH3)2].
N,N-Dimethyl(4-cyanophenyl)methaneamine (Table 2, entry 16)20
Yellow oil; yield: 120.1 mg (0.750 mmol, 75%); eluent: hexane/EtOAc/
Et2NH (30:20:1).
N,N-Dimethyl(3-methylphenyl)methanamine (Table 2, entry 10)20
Yellow oil; yield: 137.3 mg (0.920 mmol, 92%); eluent: hexane/EtOAc/
Et2NH (95:5:2).
1H NMR (400 MHz, CDCl3): δ = 7.21 (t, J = 8 Hz, 1 Harom), 7.14 (s, 1 Harom),
7.08 (t, J = 6 Hz, 2 Harom), 3.38 (s, 2 H, CH2), 2.35 (s, 3 H, ArCH3), 2.24 [s,
6 H, N(CH3)2].
13C NMR (101 MHz, CDCl3): δ = 138.8 (s, Carom), 137.8 (s, Carom), 129.8
(s, Carom), 128.1 (s, Carom), 127.8 (s, Carom), 126.2 (s, Carom), 64.4 (s, CH2),
45.4 [s, N(CH3)2], 21.4 (s, ArCH3).
1H NMR (400 MHz, CDCl3): δ = 7.62–7.60 (m, 2 Harom), 7.44–7.42 (m, 2
H
arom), 3.46 (s, 2 H, CH2), 2.24 [s, 6 H, N(CH3)2].
13C NMR (101 MHz, CDCl3): δ = 144.7 (s, Carom), 132.0 (s, Carom), 129.4
(s, Carom), 118.9 (s, Carom), 110.7 (s, Carom), 63.7 (s, CH2), 45.3 [s,
N(CH3)2].
N,N-Dimethyl(4-trifluoromethylphenyl)methanamine (Table 2,
entry 17)21
Yellow oil; yield: 156.1 mg (0.768 mmol, 77%); eluent: hexane/EtOAc/
Et2NH (95:5:2).
N,N-Dimethyl(4-methylphenyl)methanamine (Table 2, entry 11)20
Yellow oil; yield: 139.3 mg (0.933 mmol, 93%); eluent: hexane/EtOAc/
Et2NH (95:5:2).
1H NMR (400 MHz, CDCl3): δ = 7.19 (d, J = 8 Hz, 2 Harom), 7.13 (d, J = 8
Hz, 2 Harom), 3.38 (s, 2 H, CH2), 2.34 (s, 3 H, ArCH3), 2.23 [s, 6 H,
N(CH3)2].
13C NMR (101 MHz, CDCl3): δ = 136.5 (s, Carom), 135.8 (s, Carom), 129.0
(s, Carom), 128.9 (s, Carom), 64.1 (s, CH2), 45.3 [s, N(CH3)2], 21.1 (s,
ArCH3).
1H NMR (400 MHz, CDCl3): δ = 7.57 (d, J = 8 Hz, 2 Harom), 7.43 (d, J = 8
Hz, 2 Harom), 3.47 (s, 2 H, CH2), 2.25 [s, 6 H, N(CH3)2].
13C NMR (101 MHz, CDCl3): δ = 143.3 (s, Carom), 129.4 (q, J = 32 Hz,
C
arom), 129.2 (s, Carom), 125.3 (q, J = 4 Hz, Carom), 124.4 (q, J = 271 Hz,
CF3), 63.9 (s, CH2), 45.5 [s, N(CH3)2].
N,N-Dimethyl-1-phenylethan-1-amine (Table 2, entry 18)22
Yellow oil; yield: 137.1 mg (0.919 mmol, 92%); eluent: hexane/EtOAc/
Et2NH (40:10:1).
1H NMR (400 MHz, CDCl3): δ = 7.33–7.21 (m, 5 Harom), 3.24 (q, J = 7 Hz,
1 H, CH), 2.20 [s, 6 H, N(CH3)2], 1.37 (d, J = 7 Hz, 3 H, CH3).
13C NMR (101 MHz, CDCl3): δ = 144.2 (s, Carom), 128.2 (s, Carom), 127.5
(s, Carom), 126.9 (s, Carom), 66.0 (s, CHCH3), 43.3 [s, N(CH3)2], 20.3 (s,
CHCH3).
N,N-Dimethyl(4-methoxyphenyl)methanamine (Table 2, entry
12)20
Yellow oil; yield: 160.5 mg (0.971 mmol, 97%); eluent: hexane/EtOAc/
Et2NH (95:5:2).
1H NMR (400 MHz, CDCl3): δ = 7.22–7.20 (m, 2 Harom), 6.87–6.84 (m, 2
H
arom), 3.80 (s, 3 H, OCH3), 3.35 (s, 2 H, CH2), 2.22 [s, 6 H, N(CH3)2].
13C NMR (101 MHz, CDCl3): δ = 158.6 (s, Carom), 130.8 (s, Carom), 130.1
(s, Carom), 113.4 (s, Carom), 63.6 (s, CH2), 55.0 (s, OCH3), 45.1 [s, N(CH3)2].
N,N-Dimethyl-1-(4-methoxyphenyl)ethan-1-amine (Table 2, entry
19)23
Yellow oil; yield: 172.4 mg (0.962 mmol, 96%); eluent: hexane/EtOAc/
Et2NH (95:5:2).
N,N-Dimethyl(2-chlorophenyl)methanamine (Table 2, entry 13)20
Yellow oil; yield: 164.3 mg (0.968 mmol, 97%); eluent: hexane/EtOAc/
Et2NH (95:5:2).
1H NMR (400 MHz, CDCl3): δ = 7.42–7.35 (m, 2 Harom), 7.26–7.17 (m, 2
1H NMR (400 MHz, CDCl3): δ = 7.22–7.18 (m, 2 Harom), 6.87–6.84 (m, 2
H
arom), 3.80 (s, 3 H, OCH3), 3.21 (q, J = 7 Hz, 1 H, CH), 2.18 [s, 6 H,
N(CH3)2], 1.35 (d, J = 7 Hz, 3 H, CH3).
H
arom), 3.53 (s, 2 H, CH2), 2.30 [s, 6 H, N(CH3)2].
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–J