Amines Made Easily
A R T I C L E S
7.9 Hz, 2H), 1.40-1.43 (m, 2H), 1.19-1.26 (m, 6H), 0.81 (t, J ) 7.1
Hz, 3H). 13C NMR (100 MHz) δ 65.97, 58.25, 52.81, 30.79, 26.20,
25.53, 21.60, 13.04. GC-MS m/z ) 171 [M+], 156, 142, 126, 100,
84, 70, 56, 42, 29. HRMS Calcd for C10H21NO [M+] 171.16258. Found
171.16231.
1.34 (m, 2H), 1.08 (t, J ) 7.1 Hz, 6H). 13C NMR (100 MHz) δ 102.9,
88.69, 67.93, 61.21, 61.15, 44.64, 31.71, 27.63, 15.65. GC-MS (EI,
70 eV) m/z ) 219 [M+], 200, 188, 172, 126, 99, 86, 75, 41, 29. Anal.
Calcd for C11H25NO3 Anal. Calcd for C13H18ClNO C, 60.04; H, 11.49;
N, 6.39. Found C, 59.55; H, 11.15; N, 6.10.
12. N-(3-Phenylpropyl)piperidine:30 yield 72% (GC). 1H NMR (400
MHz, CDCl3) δ 7.40-7.54 (m, 5H), 2.87 (t, J ) 7.9 Hz, 2H), 2.61-
2.65 (m, 4H), 2.59 (t, J ) 7.5 Hz, 2H), 2.12 (quintet, J ) 7.9 Hz, 2H),
1.84 (quintet, J ) 5.6 Hz, 4H), 1.65-1.71 (m, 2H). 13C NMR (100
MHz, CDCl3) δ 142.7, 128.8, 128.7, 126.1, 59.43, 55.09, 34.42, 29.11,
26.47, 24.96. GC-MS (EI, 70 eV) m/z ) 203 [M+], 174, 160, 146,
117, 98, 91, 77, 70, 55, 41, 30. HRMS Calcd for C14H21N [M+]
203.16745. Found 203.16740.
13. N-[3-(4-Chlorophenyl)propyl]morpholine: yield 69% (GC). 1H
NMR (400 MHz, CDCl3) δ 7.78 (d, J ) 7.0 Hz, 2H), 7.59 (d, J ) 7.1
Hz, 2H), 3.56 (t, J ) 5.1 Hz, 4H), 3.21 (t, J ) 5.6 Hz, 4H), 2.76 (t, J
) 7.2 Hz, 2H), 2.53 (t, J ) 7.5 Hz, 2H), 1.65-1.71 (m, 2H). 13C NMR
(100 MHz, CDCl3) δ 140.8, 135.1, 128.9, 128.6, 83.41, 61.35, 57.86,
40.54, 36.72. GC-MS (EI, 70 eV) m/z ) 239 [M+], 194, 152, 125,
100, 89, 70, 56, 43, 29. Anal. Calcd for C13H18ClNO C, 65.13; H, 7.57;
N, 5.84. Found C, 64.60; H, 7.33; N, 5.66.
14. N-(4-Phenylbutyl)piperidine:31 yield 71% (GC). 1H NMR (400
MHz, CDCl3) δ 7.14-7.21 (m, 5H), 3.23 (t, J ) 5.7 Hz, 2H), 3.12 (t,
J ) 5.7 Hz, 2H), 2.63-2.71 (m, 4H), 2.15-2.34 (m, 2H), 1.90-2.08
(m, 6H), 1.78-1.86 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 142.7,
128.8, 128.7, 126.1, 67.39, 59.45, 54.23, 36.37, 29.71, 26.65, 18.94.
GC-MS (EI, 70 eV) m/z ) 217 [M+], 188, 174, 160, 124, 98, 91, 84,
70, 55, 41, 30. HRMS Calcd for C15H23N [M+] 217.15984. Found
217.16231.
5. N-Hexylthiomorpholine: yield 92% (GC). 1H NMR (400 MHz,
CDCl3) δ 3.68-3.75 (m, 4H), 3.50 (t, J ) 5.6 Hz, 4H), 2.80 (t, J )
5.6 Hz, 2H), 2.47-2.54 (m, 2H), 1.42-1.53 (m, 6H), 1.03 (t, J ) 7.1
Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 58.50, 54.10, 30.80, 27.00,
26.20, 25.60, 21.60, 13.10. GC-MS (EI, 70 eV) m/z ) 187 [M+], 126,
116, 88, 70, 57, 42, 29. Anal. Calcd for C10H21NS C, 64.22; H, 11.22;
N, 7.48; S, 17.10. Found C, 64.32; H, 11.54; N, 6.99; S, 17.43.
6. N-Hexyl-N’-benzylpiperazine:25 yield 94% (GC). 1H NMR (400
MHz, CDCl3) δ 7.24-7.34 (m, 5H), 3.55 (s, 2H), 3.37-3.41 (m, 8H),
2.83 (t, J ) 5.2 Hz, 2H), 2.35-2.55 (m, 2H), 1.47-1.55 (m, 6H), 0.88-
0.95 (t, J ) 7.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 138.6, 129.5,
128.6, 127.4, 63.53, 59.36, 53.71, 53.54, 32.22, 27.88, 27.36, 23.01,
14.56. GC-MS (EI, 70 eV) m/z ) 260 [M+], 189, 161, 146, 128, 114,
98, 91, 84, 70, 58, 42, 29. HRMS Calcd for C17H28N2 [M+] 260.22714.
Found 260.22525.
7. N-(6-Hydroxyhexyl)piperidine:26 yield 97% (GC).1H NMR (400
MHz, CDCl3) δ 3.68 (t, J ) 5.6 Hz, 2H), 3.49 (t, J ) 5.5 Hz, 2H),
3.01-3.08 (m, 4H), 2.45-2.65 (m, 2H), 1.84-1.90 (m, 2H), 1.43-
1.80 (m, 6H), 1.02-1.12 (m, 4H). 13C NMR (100 MHz, CDCl3) δ
62.70, 59.80, 55.00, 33.10, 28.10, 27.80, 26.20, 26.10, 25.50. GC-
MS (EI, 70 eV) m/z ) 185 [M+], 168, 155, 140, 124, 110, 98, 84, 70,
55, 41, 30. HRMS Calcd for C11H23NO [M+] 185.17744. Found
185.17796.
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8. N-(7-Hydroxyheptyl)piperidine:27 yield 97% (GC). H NMR
15. N-(4-Phenoxybutyl)piperidine:32 yield 90% (GC). 1H NMR
(400 MHz, CDCl3) δ 7.21-7.38 (m, 5H), 3.81 (t, J ) 5.6 Hz, 2H),
3.55 (t, J ) 5.6 Hz, 2H), 2.68-2.79 (m, 4H), 2.05-2.18 (m, 2H), 1.95-
2.09 (m, 6H), 1.85-1.97 (m, 2H). 13C NMR (100 MHz, CDCl3) δ
159.4, 129.8, 120.9, 115.1, 68.09, 59.51, 55.05, 27.97, 26.48, 26.32,
23.83. GC-MS (EI, 70 eV) m/z ) 233 [M+], 204, 149, 140, 127, 107,
98, 84, 77, 70, 55, 42, 29. HRMS Calcd for C15H23NO [M+] 233.17713.
Found 233.17796.
16. N-Hexylaniline:33 yield 76% (GC). 1H NMR (400 MHz, CDCl3)
δ 7.20-7.33 (m, 5H), 3.12 (t, J ) 5.6 Hz, 2H), 1.51-1.64 (m, 2H),
1.41-1.49 (m, 6H), 1.01 (t, J ) 6.8 Hz, 3H). 13C NMR (100 MHz,
CDCl3) δ 151.5, 125.3, 117.8, 113.7, 61.43, 28.45, 28.27, 26.31, 23.14,
14.68. GC-MS (EI, 70 eV) m/z ) 177 [M+], 148, 132, 118, 106, 93,
77, 65, 51. 41, 29. HRMS Calcd for C12H19N [M+] 177.15279. Found
177.15175.
17. N-(3-Phenylbutyl)piperidine:34 yield 88% (GC). 1H NMR (400
MHz, CDCl3) δ 7.38-7.54 (m, 5H), 2.96-3.29 (m, 1H), 2.53-2.61
(m, 4H), 2.35-2.42 (m, 2H), 2.15-2.33 (m, 2H), 1.81 (quintet, J )
5.6 Hz, 4H), 1.62-1.69 (m, 2H), 1.50 (d, J ) 7.1 Hz, 3H). 13C NMR
(100 MHz, CDCl3) δ 147.8, 128.7, 127.4, 126.3, 58.26, 55.13, 38.91,
35.84, 26.49, 24.91, 23.15. GC-MS (EI, 70 eV) m/z ) 217 [M+], 200,
174, 160, 139, 98, 91, 77, 70, 55, 41, 29. HRMS Calcd for C15H23N
[M+] 217.18148. Found 217.18304.
(400 MHz, CDCl3) δ 3.66 (t, J ) 5.6 Hz, 2H), 3.45 (t, J ) 5.5 Hz,
2H), 3.02-3.07 (m, 4H), 2.40-2.66 (m, 2H), 1.80-1.95 (m, 2H), 1.42-
1.76 (m, 6H), 0.79-0.93 (m, 6H). 13C NMR (100 MHz, CDCl3) δ
62.73, 59.95, 54.93, 33.14, 29.76, 28.10, 27.00, 26.14, 26.09, 24.75.
GC-MS (EI, 70 eV) m/z ) 199 [M+], 182, 169, 154, 140, 124, 110,
98, 84, 70, 55, 41, 31. HRMS Calcd for C12H25NO [M+] 199.19333.
Found 199.19362.
9. N-(4-Hydroxyhexyl)piperidine:28 yield 99% (GC). 1H NMR (400
MHz, CDCl3), δ 3.30 (tt, J ) 5.7, 5.6 Hz, 1H), 2.26 (t, J ) 5.6 Hz,
2H), 1.80-1.95 (m, 4H), 1.61-1.73 (m, 6H), 1.45-1.49 (m, 2H), 1.40-
1.43 (m, 2H), 1.33-1.37 (m, 2H), 0.84 (t, J ) 7.5 Hz, 3H). 13C NMR
(100 MHz, CDCl3) δ 73.1, 59.8, 54.7, 37.2, 30.8, 26.4, 25.8, 24.6,
10.5. GC-MS (EI, 70 eV) m/z ) 185 [M+], 168, 156, 138, 124, 111,
98, 84, 70, 55, 41, 29. HRMS Calcd for C11H23NO [M+] 185.17833.
Found 185.17796.
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10. N-(4,4-Diethoxybutyl)piperdine:29 yield 96% (GC). H NMR
(400 MHz, CDCl3) δ 4.44 (t, J ) 5.3 Hz, 1H), 3.85 (q, J ) 7.1 Hz,
4H), 2.24 (t, J ) 5.5 Hz, 2H), 2.13-2.18 (m, 4H), 1.55-1.63 (m, 2H),
1.37-1.51 (m, br, 6H), 1.21-1.28 (m, 2H), 1.09 (t, J ) 7.1 Hz, 6H).
13C NMR (100 MHz) δ 103.1, 61.27, 59.53, 54.95, 32.08, 26.39, 24.84,
22.55, 15.66. GC-MS (EI, 70 eV) m/z ) 229 [M+], 200, 184, 154,
138, 115, 98, 87, 71, 55, 41, 29. HRMS Calcd for C13H27NO2 [M+]
229.20309. Found 229.20418.
11. N-(4,4-Diethoxybutyl)-N-3-hydroxypropylamine: yield >99%
(GC). 1H NMR (400 MHz, CDCl3) δ 4.91 (t, J ) 5.6 Hz, 1H), 3.95 (t,
J ) 5.8 Hz, 2H), 3.75 (q, J ) 7.4 Hz, 4H), 3.05 (t, J ) 2.3 Hz, 2H),
2.91 (t, J ) 3.3 Hz, 2H), 1.63-1.78 (m, 2H), 1.48-1.51 (m, 2H), 1.26-
18. N-(3,3-Diphenylpropyl)piperidine:35 yield 60% (GC). 1H NMR
(400 MHz, CDCl3) δ 7.13-7. 42 (m, 10H), 3.91-4.05 (m, 1H), 2.75-
2.92 (m, 4H), 2.43-2.56 (m, 2H), 2.19-2.36 (m, 2H), 1.85 (quintet,
J ) 5.5 Hz, 4H), 1.59-1.73 (m, 2H). 13C NMR (100 MHz, CDCl3) δ
145.5, 128.9, 128.4, 126.6, 58.29, 55.21, 49.91, 33.40, 26.69, 25.19.
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J. AM. CHEM. SOC. VOL. 125, NO. 34, 2003 10317