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7.41 (d, J = 7.8 Hz, 1H), 7.25 (d, J = 1.5 Hz, 2H,), 7.18 (d, J = 8.1 Hz,
1H), 7.02 (t, J = 8.1 Hz, 1H), 6.94 (t, J = 7.8 Hz, 1H), 6.84 (s, 1H),
6.19 (dd, J = 1.5, 3.0 Hz, 2H), 6.09 (d, J = 3.0 Hz, 2H), 3.64 (s, 4H),
2.86 (m, 2H), 2.67 (m, 2H); 13C NMR (DEPT) (CDCl3): d 152.5
(s ꢀ 2), 142.6 (d ꢀ 2), 136.7 (s), 127.9 (s), 122.4 (d), 122.1 (d),
119.4 (d), 119.2 (d), 114.1 (s), 111.7 (d), 110.6 (d ꢀ 2), 109.6
(d ꢀ 2), 54.4 (t), 50.1 (t ꢀ 2), 23.8 (t). ESI-MS: m/z 321 ([M+H]+);
4.2.2.2. N,N-Diethyltryptamine N12-oxide (3b). Colorless thick
oil (117 mg, 95% yield). 1H NMR (CD3OD): d 7.59 (d, J = 7.8 Hz,
1H), 7.34 (d, J = 8.1 Hz, 1H), 7.14 (s, 1H), 7.10 (t, J = 8.1 Hz, 1H),
7.03 (t, J = 7.8 Hz, 1H), 3.42 (m, 2H), 3.34 (m, J = 8.3 Hz, 4H), 3.25
(m, 2H), 1.28 (m, 6H); 13C NMR (DEPT) (CD3OD): d 138.2 (s),
128.3 (s), 124.1 (d), 122.8 (d), 120.1 (d), 119.0 (d), 112.6 (d),
110.4 (s), 65.4 (t), 60.6 (t ꢀ 2), 20.0 (t), 8.7 (q ꢀ 2). ESI-MS: m/z
233 ([M+H]+); HR-ESI-MS: calcd for C14H21N2O ([M+H]+)
233.1654, found 233.1653.
HR-ESI-MS: calcd for
321.1602.
C
20H21N2O2 ([M+H]+) 321.1603, found
4.2.1.11. N,N-Bis(thiophen-2-yl-methyl)tryptamine (2k). Color-
less thick oil (362 mg, 82% yield). 1H NMR (CDCl3): d 7.50 (br s,
1H), 7.12 (d, J = 7.7 Hz, 1H), 6.94 (d, J = 8.2 Hz, 1H), 6.86 (dd,
J = 4.2, 2.0 Hz, 2H), 6.79 (t, J = 8.2 Hz, 1H), 6.70 (t, J = 7.7 Hz, 1H),
6.62 (s, 1H), 6.56–6.59 (m, 4H), 3.57 (s, 4H), 2.64 (m, 2H), 2.51
(m, 2H); 13C NMR (DEPT) (CDCl3): d 142.8 (s ꢀ 2), 136.2 (s), 127.6
(s), 126.6 (d ꢀ 2), 125.9 (d ꢀ 2), 124.9 (d ꢀ 2) 121.9 (d), 121.8 (d),
119.2 (d), 118.9 (d), 114.2 (s), 111.2 (d), 53.6 (t), 52.2 (t ꢀ 2),
23.6 (t). ESI-MS: m/z 353 ([M+H]+); HR-ESI-MS: calcd for
4.2.2.3. N,N-Dipropyltryptamine N12-oxide (3c). Colorless thick
oil (117 mg, 85% yield). 1H NMR (CDCl3): d 10.22 (br s, 1H), 7.52
(d, J = 7.8 Hz, 1H), 7.40 (d, J = 8.0 Hz, 1H), 7.14 (t, J = 8.0 Hz, 1H),
7.06 (t, J = 7.8 Hz, 1H), 6.95 (s, 1H), 3.40 (m, 2H), 3.24 (m, 2H),
3.18 (m, 4H), 1.80 (m, 4H), 0.94 (t, J = 7.5 Hz, 6H); 13C NMR (DEPT)
(CDCl3): d 136.7 (s), 127.1 (s), 123.0 (d), 121.9 (d), 119.2 (d), 118.1
(d), 112.0 (d), 110.1 (s), 67.6 (t ꢀ 2), 66.0 (t), 19.4 (t), 16.8 (t ꢀ 2),
11.3 (q ꢀ 2). ESI-MS: m/z 261 ([M+H]+); HR-ESI-MS: calcd for
C16H25N2O ([M+H]+) 261.1967, found 261.1970.
C
20H21N2S2 ([M+H]+) 353.1146, found 353.1143.
4.2.2.4. N,N-Diisobutyltryptamine
N
12-oxide (3d). Colorless
7.49 (d,
thick oil (130 mg, 85% yield). 1H NMR (CDCl3):
d
4.2.1.12. N,N-Bis(2,4,5-trimethoxybenzyl)tryptamine (2l). Col-
orless thick oil (545 mg, 84% yield). 1H NMR (C5D5N): d 12.2 (br
s, 1H), 7.64 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.44 (s, 1H),
7.34 (s, 2H), 7.31 (t, J = 7.5 Hz, 1H), 7.14 (t, J = 7.5 Hz, 1H), 6.60 (s,
2H), 3.84 (s, 6H), 3.82 (s, 6H), 3.79 (m, 4H), 3.57 (s, 6H), 3.57 (m,
2H), 3.46 (m, 2H); 13C NMR (DEPT) (C5D5N): d 153.1 (d ꢀ 4),
144.4 (s ꢀ 2), 138.1 (s), 128.1 (s), 124.8 (d), 122.5 (d), 119.8 (d),
119.2 (d), 116.9 (s ꢀ 2), 116.9 (d ꢀ 2), 112.6 (d), 110.1 (s), 98.4
(d ꢀ 2), 57.2 (t ꢀ 2), 56.6 (t ꢀ 2), 56.4 (t ꢀ 2), 54.7 (t), 53.9 (t ꢀ 2),
22.5 (t). ESI-MS: m/z 521 ([M+H]+); HR-ESI-MS: calcd for
J = 7.7 Hz, 1H), 7.42 (d, J = 7.7 Hz, 1H), 7.13 (t, J = 7.7 Hz, 1H), 7.05
(t, J = 7.7 Hz, 1H), 6.93 (s, 1H), 3.52 (m, 2H), 3.22 (m, 2H), 3.19 (d,
J = 5.2 Hz, 4H), 2.28 (m, 2H), 1.13 (d, J = 6.5 Hz, 6H), 1.11 (d,
J = 6.5 Hz, 6H); 13C NMR (DEPT) (CDCl3): d 136.5 (s), 126.7 (s),
122.8 (d), 121.1 (d), 118.4 (d), 117.5 (d), 111.8 (d), 108.7 (s), 73.7
(t ꢀ 2), 66.0 (t), 49.2 (d ꢀ 2), 23.9 (q ꢀ 2), 22.7 (q ꢀ 2) 19.6 (t).
ESI-MS: m/z 289 ([M+H]+), 577 ([2M+H]+); HR-ESI-MS: calcd for
C
18H29N2O ([M+H]+) 289.2280, found 289.2281.
C
30H37N2O6 ([M+H]+) 521.2652, found 521.2651.
4.2.2.5. N,N-Diisopentyltryptamine
N
12-oxide (3e). Colorless
thick oil (139 mg, 83% yield). 1H NMR (CDCl3): d 10.14 (br s, 1H),
7.54 (d, J = 7.6 Hz, 1H), 7.41 (d, J = 7.6 Hz, 1H), 7.16 (t, J = 7.8 Hz,
1H), 7.09 (t, J = 7.8 Hz, 1H), 6.99 (s, 1H), 3.42 (m, 2H), 3.29 (m,
2H), 3.24 (m, 4H), 1.72 (m, 4H), 1.61 (m, 2H), 0.93 (br d,
J = 6.3 Hz, 12H); 13C NMR (DEPT) (CDCl3): 136.9 (s), 127.1 (s),
123.2 (d), 109.8 (s), 121.6 (d), 118.9 (d), 118.0 (d), 112.1 (d), 64.9
(t ꢀ 2), 66.1 (t), 31.9 (t ꢀ 2), 26.6 (d ꢀ 2), 22.7 (q ꢀ 4), 19.4 (t).
ESI-MS: m/z 317 ([M+H]+), 633 ([2M+H]+); HR-ESI-MS: calcd for
4.2.1.13. N,N-Bis(3-nitrobenzyl)tryptamine (2m). Colorless
thick oil (430 mg, 80% yield). 1H NMR (CDCl3): d 8.16 (br s, 2H),
8.04 (d, J = 8.4 Hz, 2H), 7.99 (br s, 1H), 7.61 (d, J = 7.5 Hz, 2H),
7.41 (d, J = 7.5 Hz, 1H), 7.38 (d, J = 7.5 Hz, 1H), 7.29 (t, J = 8.4 Hz,
2H), 7.15 (t, J = 6.9 Hz, 1H), 6.98 (s, 1H), 6.97 (t, J = 6.9 Hz, 1H),
3.75 (br s, 4H), 2.99 (m, 2H), 2.85 (m, 2H); 13C NMR (DEPT) (CDCl3):
d 148.1 (s ꢀ 2), 141.5 (s ꢀ 2), 136.2 (s), 134.6 (d ꢀ 2), 129.2 (d ꢀ 2),
127.1 (s), 123.4 (d ꢀ 2), 122.1 (d ꢀ 2), 121.9 (d), 121.7 (d), 119.1
(d),118.4 (d), 113.7 (s), 111.2 (d), 57.7 (t ꢀ 2), 53.9 (t), 23.3 (t).
ESI-MS: m/z 431 ([M+H]+); HR-ESI-MS: calcd for C24H23N4O4
([M+H]+) 431.1719, found 431.1718.
C
20H33N2O ([M+H]+) 317.2593, found 317.2590.
4.2.2.6. N,N-Dicyclopropylmethyltryptamine
N
12-oxide
(3f). Colorless thick oil (123 mg, 82% yield). 1H NMR (CDCl3): d
10.29 (br s, 1H), 7.55 (d, J = 7.8 Hz, 1H), 7.41 (d, J = 7.8 Hz, 1H),
7.12 (t, J = 7.0 Hz, 1H), 7.07 (t, J = 7.0 Hz, 1H), 7.00 (s, 1H), 3.67
(m, 2H), 3.32 (m, 2H), 3.25 (m, 4H), 1.34 (m, 2H), 0.71 (m, 4H),
0.35 (m, 4H); 13C NMR (DEPT) (CDCl3): d 136.8 (s), 127.2 (s),
123.1 (d), 121.5 (d), 118.8 (d), 118.1 (d), 112.0 (d), 109.9 (s), 71.1
(t ꢀ 2), 64.8 (t), 19.3 (t), 5.7 (d ꢀ 2), 4.8 (t ꢀ 2), 4.3 (t ꢀ 2). ESI-
MS: m/z 285 ([M+H]+), 569 ([2M+H]+); HR-ESI-MS: calcd for
C18H25N2O ([M+H]+) 285.1967, found 285.1965.
4.2.2. General procedure for the preparation of compounds
3a–k
m-Chloroperoxybenzoic acid (138 mg, 0.80 mmol) in CHCl3
(10 mL) was added at 0 °C to a stirred solution of N,N-dimethyl-
tryptamine (2a) (100 mg, 0.53 mmol) or other N,N-dialkyltrypta-
mine derivatives (0.53 mmol) in CHCl3 under argon. After 10 min,
the reaction mixture was poured into a saturated solution of
Na2CO3 and the N12-oxides were extracted with CHCl3. The organic
layer was washed with water and brine, dried over Na2SO4, and
concentrated in vacuum. The crude product was purified by CC of
silica gel with gradient CHCl3/MeOH as eluant afforded compounds
4.2.2.7.
N,N-Dicyclohexylmethyltryptamine
N12-oxide
(3g). Colorless thick oil (160 mg, 82% yield). 1H NMR (CDCl3): d
10.56 (br s, 1H), 7.49 (d, J = 7.6 Hz, 1H), 7.43 (d, J = 7.6 Hz, 1H),
7.14 (d, J = 7.7 Hz, 1H), 7.06 (t, J = 7.7 Hz, 1H), 6.93 (s, 1H), 3.52
(m, 2H), 3.22 (m, 2H), 3.16 (m, 4H), 1.93–1.99 (m, 6H, overlapped),
1.60–1.71 (m, 6H, overlapped), 1.05–1.30 (m, 10H, overlapped);
13C NMR (DEPT) (CDCl3, 100 MHz): d 136.6 (s), 126.8 (s), 122.8
(d), 121.4 (d), 118.7 (d), 117.6 (d), 112.0 (d), 108.8 (s), 73.1
(t ꢀ 2), 65.8 (t), 33.3 (t ꢀ 4), 33.2 (t ꢀ 4), 32.9 (d ꢀ 2), 25.6
(t ꢀ 2), 19.8 (t). ESI-MS: m/z 369 ([M+H]+), 737 ([2M+H]+); HR-
3a–k
.
4.2.2.1. N,N-Dimethyltryptamine N12-oxide (3a). White solid
(105 mg, 98% yield). 1H NMR (CD3OD): d 8.50 (br s, 1H), 7.59 (d,
J = 7.7 Hz, 1H), 7.31 (d, J = 8.0 Hz, 1H), 7.15 (s, 1H), 7.11 (t,
J = 8.0 Hz, 1H), 7.03 (t, J = 7.7 Hz, 1H), 3.72 (m, 2H), 3.34 (s, 6H),
3.28 (m, 2H); 13C NMR (DEPT) (CD3OD): d 138.7 (s), 128.8 (s),
124.3 (d), 123.1 (d), 120.4 (d), 119.6 (d), 112.9 (d), 111.2 (s), 72.4
(t), 58.9 (q ꢀ 2), 21.1 (t). ESI-MS: m/z 205 ([M+H]+); HR-ESI-MS:
calcd for C12H17N2O ([M+H]+) 205.1341, found 205.1343.
ESI-MS: calcd for
369.2905.
C
24H37N2O ([M+H]+) 369.2906, found