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1H). ESI-MS: m/z = 257 [M + 1]+. Anal. Calcd. for C16H20N2O: C,
74.97; H, 7.86; N, 10.93. Found: C, 74.67; H, 7.77; N, 10.83.
Purification: silica gel column chromatography using PE / EtOAc
(10 : 1). Brown oil (45%). H-NMR (CDCl3, 400 M, d): 7.67 (d, J =
1
8.0 Hz, 1H), 7.44 (t, J = 8.0 Hz, 1H), 7.39 (m, 6H), 7.19 (d, J = 8.0 Hz,
1H), 4.08 (s, 3H), 3.74 (d, J = 13.2 Hz, 1H), 3.51 (d, J = 13.2 Hz, 1H),
3.07 (m, 1H), 2.98 (m, 3H), 2.72 (m, 1H), 2.55 (m, 1H), 2.31 (s, 3H),
2.20 (m, 1H). ESI-MS: m/z =333 [M + 1]+. Anal. Calcd. for C22H24N2O:
C, 79.48; H, 7.28; N, 8.43. Found: C, 79.73; H, 7.57; N, 8.26.
2-Ethyl(methyl)aminomethyl-9-methyl-1,2,3,4-
tetrahydrocarbazole-1-one 5b
Reagents: 9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 4a, paraf-
ormaldehyde, and ethylmethyl- amine hydrochloride 6b. Purifi-
cation: silica gel column chromatography using PE / EtOAc /
1
Et3N (50 : 20 : 1). Yellow solid (74%), m.p.: 154–1568C. H-NMR
2-Benzyl(cyanoethyl)aminomethyl-9-methyl-1,2,3,4-
tetrahydrocarbazole-1-one 5g
(CDCl3, 400 M, d): 7.67 (d, J = 8.0 Hz, 1H), 7.44 (t, J = 8.0 Hz, 1H),
7.36 (d, J = 8.0 Hz, 1H), 7.18 (t, J = 8.0 Hz, 1H), 4.13 (s, 3H), 3.18 (m,
1H), 3.10 (m, 2H), 2.95 (m, 1H), 2.85 (m, 1H), 2.71 (m, 1H), 2.57 (s,
3H), 2.17 (m, 1H), 1.31 (m, 5H). ESI-MS: m/z = 271 [M + 1]+. Anal.
Calcd. for C17H22N2O: C, 75.52; H, 8.20; N, 10.36. Found: C, 75.35;
H, 7.97; N, 10.48.
Reagents: 9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 4a, paraf-
ormaldehyde, and N-benzyl-2- cyanoethylamine hydrochloride
6g. Purification: silica gel column chromatography using PE /
EtOAc (10 : 1). Brown oil (50%). 1H-NMR (CDCl3, 400 M, d): 7.66 (d,
J = 8.0 Hz, 1H), 7.42 (m, 7H), 7.19 (t, J = 8.0 Hz, 1H), 4.07 (s, 3H),
3.88 (d, J = 13.2 Hz, 1H), 3.57 (d, J = 13.2 Hz, 1H), 3.11 (m, 1H), 3.00
(m, 3H), 2.83 (m, 1H), 2.77 (t, J = 6.8 Hz, 2H), 2.54 (m, 3H), 2.10 (m,
1H). ESI-MS: m/z =372 [M + 1]+. Anal. Calcd. for C24H25N3O: C,
77.60; H, 6.78; N, 11.31. Found: C, 77.37; H, 6.67; N, 11.68.
2-Diethylaminomethyl-9-methyl-1,2,3,4-
tetrahydrocarbazole-1-one 5c
Reagents: 9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 4a, paraf-
ormaldehyde, and diethylamine hydrochloride 6c. Purification:
silica gel column chromatography using PE / EtOAc / Et3N
(100 : 50 : 1). Yellow oil (60%). 1H-NMR (CDCl3, 400 M, d): 7.65 (d, J
= 8.0 Hz, 1H), 7.41 (t, J = 8.0 Hz, 1H), 7.34 (d, J = 8.0 Hz, 1H), 7.16 (t,
J = 8.0 Hz, 1H), 4.05 (s, 3H), 3.14 (m, 3H), 2.81 (m, 6H), 2.51 (m,
1H), 2.14 (m, 1H), 1.09 (t, J = 7.2 Hz, 6H). ESI-MS: m/z = 285 [M + 1]+.
Anal. Calcd. for C18H24N2O: C, 76.02; H, 8.51; N, 9.85. Found: C,
75.85; H, 8.23; N, 9.68.
2-(1H-Imidazol-1-ylmethyl)-9-methyl-1,2,3,4-
tetrahydrocarbazole-1-one 5h
Reagents: 9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 4a, paraf-
ormaldehyde, and 1H-imidazole hydrochloride 6h. Purification:
silica gel column chromatography using PE / EtOAc / EtOH
1
(10 : 10 : 1). Yellow solid (82%), m.p.: 56–588C. H-NMR (CDCl3,
400 M, d): 7.51 (d, J = 8.0 Hz, 1H), 7.45 (s, 1H), 7.32 (t, J = 8.0 Hz,
1H), 7.22 (d, J = 8.0 Hz, 1H), 7.05 (t, J = 8.0 Hz, 1H), 7.00 (s, 1H),
6.95 (s, 1H), 4.30 (d, J = 5.6 Hz, 2H), 3.96 (s, 3H), 3.02 (m, 1H), 2.83
(m, 2H), 2.08 (m, 1H), 1.74 (m, 1H). ESI-MS: m/z = 280 [M + 1]+.
Anal. Calcd. for C17H17N3O: C, 73.10; H, 6.13; N, 15.04. Found: C,
73.27; H, 6.25; N, 15.35.
2-(29-Ethoxy-29-oxo-N-methyl)ethylaminomethyl-9-
methyl-1,2,3,4-tetrahydrocarbazole-1-one 5d
Reagents: 9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 4a, paraf-
ormaldehyde, and sarcosine ethyl ester hydrochloride 6d (pre-
pared according to ref. [36]). Purification: silica gel column chro-
matography using PE / Et3N (40 : 1). Yellow oil (34%). 1H-NMR
(CDCl3, 400 M, d): 7.66 (d, J = 8.0 Hz, 1H), 7.42 (t, J = 8.0 Hz, 1H),
7.35 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 1H), 4.21 (q, J = 7.2 Hz,
2H), 4.05 (s, 3H), 3.46 (d, J = 16.8 Hz, 1H), 3.36 (d, J = 16.8 Hz, 1H),
3.17 (m, 2H), 3.02 (m, 1H), 2.81 (m, 2H), 2.50 (s, 3H), 2.47 (m, 1H),
2.18 (m, 1H), 1.30 (t, J = 7.2 Hz, 3H). ESI-MS: m/z =329 [M + 1]+.
Anal. Calcd. for C19H24N2O3: C, 69.49; H, 7.37; N, 8.53. Found: C,
69.26; H, 7.46; N, 8.63.
2-(Piperidin-1-ylmethyl)-9-methyl-1,2,3,4-
tetrahydrocarbazole-1-one 5i
Reagents: 9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 4a, paraf-
ormaldehyde, and piperidine hydrochloride 6i. Purification:
silica gel column chromatography using PE / EtOAc (2 : 1). Brown
oil (35%). 1H-NMR (CDCl3, 400 M, d): 7.66 (d, J = 8.0 Hz, 1H), 7.42 (t,
J = 8.0 Hz, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 1H), 4.05
(s, 3H), 3.15 (m, 1H), 3.01 (m, 2H), 2.89 (m, 1H), 2.61 (m, 6H), 2.15
(m, 1H), 1.70 (m, 4H), 1.51 (m, 2H). ESI-MS: m/z =297 [M + 1]+. Anal.
Calcd. for C19H24N2O: C, 76.99; H, 8.16; N, 9.45. Found: C, 76.75;
H, 8.35; N, 9.44.
2-Cyclohexyl(methyl)aminomethyl-9-methyl-1,2,3,4-
tetrahydrocarbazole-1-one 5e
Reagents: 9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 4a, paraf-
ormaldehyde, and N-methyl- cyclohexanamine hydrochloride
6e. Purification: silica gel column chromatography using PE /
EtOAc (1 : 1). Brown oil (22%). 1H-NMR (CDCl3, 400 M, d): 7.66 (d, J
= 8.0 Hz, 1H), 7.42 (t, J = 8.0 Hz, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.16 (t,
J =8.0 Hz, 1H), 4.05 (s, 3H), 3.15 (m, 1H), 3.06 (m, 1H), 2.96 (m,
1H), 2.82 (m, 1H), 2.72 (m, 1H), 2.62 (m, 1H), 2.47 (s, 3H), 2.15 (m,
1H), 2.03 (m, 1H), 1.91 (m, 4H), 1.39 (m, 6H). ESI-MS: m/z =325 [M +
1]+. Anal. Calcd. for C21H28N2O: C, 77.74; H, 8.70; N, 8.63. Found:
C, 77.46; H, 8.47; N, 8.68.
2-(Pyrrolidin-1-ylmethyl)-9-methyl-1,2,3,4-
tetrahydrocarbazole-1-one 5j
Reagents: 9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 4a, paraf-
ormaldehyde, and pyrrolidine hydrochloride 6j. Purification:
silica gel column chromatography using PE / EtOAc / EtOH
1
(10 : 10 : 1). Yellow solid (28%), m.p.: 69–708C. H-NMR (CDCl3,
400 M, d): 7.55 (d, J = 8.0 Hz, 1H), 7.34 (t, J = 8.0 Hz, 1H), 7.24 (d, J =
8.0 Hz, 1H), 7.07 (t, J = 8.0 Hz, 1H), 3.92 (s, 3H), 3.70 (m, 1H), 3.41
(m, 3H), 3.13 (m, 3H), 2.98 (m, 2H), 2.09 (m, 4H), 1.94 (m, 1H), 1.15
(m, 1H). ESI-MS: m/z =283 [M + 1]+. Anal. Calcd. for C18H22N2O: C,
76.56; H, 7.85; N, 9.92. Found: C, 76.35; H, 7.83; N, 9.85.
2-Benzyl(methyl)aminomethyl-9-methyl-1,2,3,4-
tetrahydrocarbazole-1-one 5f
Reagents: 9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 4a, paraf-
ormaldehyde, and N-methylbenzyl- amine hydrochloride 6f.
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