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X.-J. YIN ET AL.
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N-Ethyl-N-Piperazinyl-3-indolylmethylamine (12): Yellow oil, yield 93%. H NMR
(400 MHz, CDCl3) δH: 9.60 (s, 1H, NH), 7.75-7.01 (m, 5H, H-2, 4, 5, 6, 7), 3.74 (s, 2H,
CH2 N), 2.96-2.70 (m, 4H, H-2′, 6′), 1.83-1.75 (m, 2H, CH2CH3), 1.83–1.75 (m, 4H, H-3′,
5′), 1.17 (d, 3H, CH2CH3). 13C NMR (100 MHz, CDCl3) δ: 136.3 (C-8), 128.2 (C-9), 124.3
(C-2), 121.7 (C-6), 119.4 (C-5), 119.3 (C-4), 111.5 (C-3), 111.2 (C-7), 61.1 (C-3′, 5′), 53.7
(CH2 N), 53.4 (C-2′, 6′), 50.6 (C-1″), 20.1 (C-2″). ESIMS: m/z 244 [M + H]+; HRESIMS:
m/z 244.1705 [M + H]+ (calcd for C15H21N3, 244.1808).
N-(2″-Hydroxyethyl)-N-Piperazinyl-3-indolylmethylamine (13): White amorphous
powder, mp 86–87 °C, yield 83%.
N-(2″-Methoxyethyl)-N-Piperazinyl-3-indolylmethylamine (14): Yellow oil, yield 85%.
1H NMR (400 MHz, CDCl3) δH: 9.71 (s, 1H, NH), 7.73-6.94 (m, 5H, 5H, H-2, 4, 5, 6, 7),
3.76 (s, 2H, CH2 N), 3.51-3.49 (m, 2H, CH2CH2OCH3), 3.32 (s, 3H, CH2CH2OCH3), 2.69-
2.57 (m, 10H, H-1″, 2′, 3′, 5′, 6′). 13C NMR (100 MHz, CDCl3) δ: 136.3 (C-8), 128.3 (C-9),
124.6 (C-2), 121.6 (C-6), 119.3 (C-5), 119.2 (C-4), 111.4 (C-3), 111.1 (C-7), 70.0 (C-2″),
58.8 (OCH3), 57.8 (C-3′, 5′), 53.5 (CH2 N), 53.1 (C-2′, 6′), 52.6 (C-1″). ESIMS: m/z 274
[M + H]+; HRESIMS: m/z 274.1810 [M + H]+ (calcd for C16H23N3O, 274.1914).
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N-Aminoethyl-N-Piperazinyl-3-indolylmethylamine (15): Yellow oil, yield 80%. H
NMR (400 MHz, CDCl3) δH: 8.38 (s, 1H, NH), 7.73-7.10 (m, 5H, H-2, 4, 5, 6, 7), 3.74
(s, 2H, CH2 N), 2.79-2.17 (m, 14H, 2-aminoethylpiperazinyl-H). 13C NMR (100 MHz,
CDCl3) δ: 136.1 (C-8), 128.0 (C-9), 123.8 (C-2), 121.9 (C-6), 119.4 (C-5), 119.4 (C-4),
112.1 (C-3), 111.0 (C-7), 60.7 (CH2CH2 NH2), 53.2 (CH2N), 53.2 (C-3′, 5′), 52.9 (C-2′, 6′),
38.6 (CH2CH2NH2). ESIMS: m/z 259 [M + H]+; HRESIMS: m/z 259.1841 [M + H]+ (calcd
for C15H22N4, 259.1917).
N-Isopropyl-N-piperazinyl-3-indolylmethylamine (16): White amorphous powder, mp
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118-119 °C, yield 93%. H NMR (400 MHz, CDCl3) δH: 9.57 (s, 1H, NH), 7.73-6.94 (m,
5H, H-2, 4, 5, 6, 7), 3.78 (s, 2H, CH2 N), 2.69-2.60 (m, 9H, H-1″, 2′, 3′, 5′, 6′), 1.05 (d, 6H,
Me). 13C NMR (100 MHz, CDCl3) δ: 136.2 (C-8), 128.3 (C-9), 124.4 (C-2), 121.7 (C-6),
119.3 (C-5), 119.3 (C-4), 111.3 (C-3), 111.2 (C-7), 54.5 (C-1″), 53.1 (CH2 N), 53.1 (C-3′, 5′),
48.7 (C-2′, 6′), 18.7 (C-Me). ESIMS: m/z 258 [M + H]+; HRESIMS: m/z 258.1862 [M + H]+
(calcd for C16H23N3, 258.1965).
N-Acetyl-N-Piperazinyl-3-indolylmethylamine (17): White amorphous powder, mp
116–116.5 °C, yield 97%.
N-tert-Butyloxycarbonyl-N-Piperazinyl-3-indolylmethylamine (18): White amor-
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phous powder, mp 160–161 °C, yield 96%. H NMR (400 MHz, CDCl3) δH: 8.93 (s,
1H, NH), 7.77-7.07 (m, 5H, H-2, 4, 5, 6, 7), 3.77 (s, 2H, CH2 N), 3.48 (m, 4H, H-3′,
5′), 2.51-2.49 (m, 4H, H-2′, 6′), 1.50 (s, 9H, Me-Boc). 13C NMR (100 MHz, CDCl3) δ:
154.9 (CO), 136.3 (C-8), 127.9 (C-9), 124.1 (C-2), 121.9 (C-6), 119.4 (C-5), 119.4 (C-4),
111.6 (C-3), 111.2 (C-7), 79.7 (C-Boc), 53.5 (CH2 N), 52.7 (C-2′, 6′), 45.0 (C-3′, 5′),
28.4 (C-Boc). ESIMS: m/z 316 [M + H]+; HRESIMS: m/z 316.1952 [M + H]+ (calcd for
C18H25N3O2, 316.2020).
N-Homopiperazinyl-3-indolylmethylamine (20): Yellow oil, yield 76%.
N-Methyl-N-homopiperazinyl-3-indolylmethylamine (21): Yellow oil, yield 80%.1H
NMR (400 MHz, CDCl3) δH: 10.05 (s, 1H, NH), 7.80-7.02 (m, 5H, H-2, 4, 5, 6, 7), 3.89 (s,
2H, CH2 N), 2.89-2.85 (m, 4H, H-2′, 4′), 2.75-2.69 (m, 4H, H-6′, 7′), 2.40 (s, 3H, NMe),
1.89-1.85 (m, 2H, H-3′). 13C NMR (100 MHz, CDCl3) δ: 136.4 (C-8), 128.1 (C-9), 124.3
(C-2), 121.6 (C-6), 119.4 (C-5), 119.1 (C-4), 112.6 (C-3), 111.3 (C-7), 57.5 (C-6′), 56.8 (C-7′),