C. B. Singh, V. Kavala, A. K. Samal, B. K. Patel
FULL PAPER
(2-Fluorophenyl)octylamine (3e): Yield: 0.357 g (80%). 1H NMR
(400 MHz, CDCl3): δ = 0.88 (t, J = 7.2 Hz, 3 H), 1.27–1.49 (br. s,
10 H), 1.66 (m, 2 H), 3.12 (t, J = 7.2 Hz, 2 H), 3.89 (br. s, 1 H),
6.58 (m, 1 H), 6.67 (m, 1 H), 6.97 (m, 1 H) ppm.13C NMR
(100 MHz, CDCl3): δ = 14.3, 22.8, 27.3, 29.4, 29.6, 29.7, 32.0, 43.8,
112.1, 112.2, 114.4, 114.5, 116.3, 116.4, 124.7, 124.8, 137.1, 137.2,
(318.26): calcd. C 64.16, H 6.33, N 4.40; found C 64.36, H 6.39, N
4.37.
Butyl(4-nitrobenzyl)phenylamine(1j): Yield: 0.539 g (95%). 1H
NMR (400 MHz, CDCl3): δ = 0.95 (t, J = 7.2 Hz, 3 H), 1.36 (m,
2 H), 1.62 (m, 2 H), 3.40 (t, J = 8.0 Hz, 2 H), 4.59 (s, 2 H), 6.59
(d, J = 8 Hz, 2 H), 6.67 (t, J = 7.2 Hz, 1 H), 7.15 (t, J = 7.2 Hz, 2
H), 7.35 (d, J = 8.4 Hz, 2 H), 8.12 (d, J = 8.4 Hz, 2 H) ppm. 13C
NMR (100 MHz, CDCl3): δ = 14.2, 20.5, 29.5, 51.7, 54.6, 112.5,
150.5, 152.8 ppm. IR (KBr): ν = 3445, 3020, 2950, 2929, 2858,
˜
1621, 1524, 1340, 1257, 1189, 1102, 1031, 913, 743 cm–1. C14H22FN
(223.34): calcd. C 75.19, H 9.93, N 6.27; found C 74.97, H 9.89, N
6.27.
116.9, 124.0, 127.4, 129.5, 147.2, 147.6, 148.1 ppm. IR (KBr): ν =
˜
3062, 3046, 2958, 2932, 2872, 1598, 1505, 1343, 1250, 1222, 1195,
1110, 932, 858, 806, 748, 735, 693 cm–1. C17H20N2O2 (284.36):
calcd. C 71.81, H 7.09, N 9.85; found C 72.06, H 7.24, N 9.75.
(4-Bromophenyl)octylamine (6e): Yield: 0.477 g (84%). 1H NMR
(400 MHz, CDCl3): δ = 0.89 (t, J = 6.8 Hz, 3 H), 1.26–1.37 (br. s,
10 H), 1.56 (m, 2 H), 3.04 (t, J = 7.2 Hz, 2 H), 3.59 (br. s, 1 H),
6.44 (d, J = 8.8 Hz, 2 H), 7.22 (d, J = 8.8 Hz, 2 H) ppm.13C NMR
(100 MHz, CDCl3): δ = 14.2, 22.8, 26.3, 29.4, 29.5, 29.7, 29.9, 31.8,
(4-Bromophenyl)butyl(4-nitrobenzyl)amine (6j): Yield: 0.689 g
(95%). 1H NMR (400 MHz, CDCl3): δ = 0.94 (t, J = 7.2 Hz, 3 H),
1.35 (m, 2 H), 1.62 (m, 2 H), 3.89 (t, J = 7.6 Hz, 2 H), 4.58 (s, 2
H), 6.46 (d, J = 8.8 Hz, 2 H), 7.21 (d, J = 8.8 Hz, 2 H), 7.34 (d, J
= 8.8 Hz, 2 H), 8.12 (d, J = 8.8 Hz, 2 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 14.1, 20.4, 29.4, 51.8, 54.5, 108.7, 114.0,
44.2, 108.6, 114.3, 132.0, 147.6 ppm. IR (KBr): ν = 3445, 3020,
˜
2950, 2929, 2858, 1621, 1524, 1340, 1257, 1189, 1102, 1031, 913,
743 cm–1. C14H22BrN (284.24): calcd. C 59.16, H 7.80, N 4.93;
found C 59.86, H 7.50, N 5.23.
124.0, 127.3, 132.1, 146.8, 147.0, 147.2 ppm. IR (KBr): ν = 3064,
˜
(2,4-Dimethylphenyl)octylamine(7e): Yield: 0.396 g (85%). 1H
NMR (400 MHz, CDCl3): δ = 0.96 (t, J = 7.2 Hz, 3 H), 1.37–1.49
(br. s, 10 H), 1.68 (m, 2 H), 2.16 (s, 3 H), 2.28 (s, 3 H), 3.16 (t, J
= 7.2 Hz, 2 H), 6.58 (d, J = 8.0 Hz, 1 H), 6.91 (s, 1 H), 6.97 (d, J
= 8.0 Hz, 1 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 14.4, 17.7,
20.6, 22.9, 27.2, 29.9, 31.9, 44.5, 110.0, 121.9, 125.8, 127.4, 130.9,
3032, 2958, 2931, 2872, 1597, 1505, 1342, 1280, 1222, 1195, 1174,
1110, 932, 806, 734 cm–1. C17H19BrN2O2 (363.26): calcd. C 56.21,
H 5.27, N 7.71; found C 56.60, H 5.05, N 7.51.
Allyl(phenyl)butylamine (1k): Yield: 0.340 g (90%). 1H NMR
(400 MHz, CDCl3): δ = 0.99 (t, J = 7.6 Hz, 3 H), 1.34 (m, 2 H),
1.55 (m, 2 H), 3.24 (m, 2 H), 3.88 (m, 2 H), 5.13 (m, 2 H), 5.82
(m, 1 H), 6.63 (m, 3 H), 7.18 (m, 2 H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 14.2, 20.5, 29.5, 50.7, 50.9, 53.3, 111.8, 112.1, 115.2,
144.2 ppm. IR (KBr): ν = 3423, 2923, 2857, 1615, 1514, 1465, 1308,
˜
1267, 1146, 803, 751 cm–1. C16H27N (233.40): calcd. C 82.34, H
11.66, N 6.00; found C 82.54, H 11.46, N 6.07.
115.8, 134.5, 148.3, 148.5 ppm. IR (KBr): ν = 3065, 3026, 2958,
˜
Diallyl(4-bromophenyl)amine(6h): Yield: 0.413 g (82%). 1H NMR
(400 MHz, CDCl3): δ = 3.85 (m, 4 H), 5.11 (m, 4 H), 5.77 (m, 2
H), 6.51 (d, J = 7.6 Hz, 2 H), 7.20 (d, J = 9.2 Hz, 2 H) ppm.13C
NMR (100 MHz, CDCl3): δ = 53.1, 108.2, 114.1, 116.3, 131.8,
2833, 2873, 1598, 1505, 1364, 1287, 1120, 1187, 988, 917, 745,
691 cm–1. C13H19N (189.30): calcd. C 82.48, H 10.12, N 7.40; found
C 82.39, H 10.06, N 7.46.
Allyl(4-bromophenyl)butylamine (6k): Yield: 0.466 g (87%). 1H
NMR (400 MHz, CDCl3): δ = 0.93 (t, J = 7.2 Hz, 3 H), 1.32 (m,
2 H), 1.55 (m, 2 H), 3.24 (t, J = 7.6 Hz, 2 H), 3.86 (d, J = 4.4 Hz,
2 H), 5.11 (m, 2 H), 5.78 (m, 1 H), 6.48 (d, J = 8.8 Hz, 2 H), 7.22
(d, J = 8.8 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 14.2,
20.5, 29.5, 50.9, 53.4, 107.6, 113.7, 116.2, 131.9, 133.8, 147.5 ppm.
133.6, 147.7 ppm. IR (KBr): ν = 3081, 2981, 2929, 2862, 1592,
˜
1498, 1388, 1233, 1180, 992, 920, 806, 750 cm–1. C12H14BrN
(252.16): calcd. C 57.16, H 5.60, N 5.55; found C 57.36, H 5.40, N
5.44.
Diallyl(2,4-dimethylphenyl)amine(7h): Yield: 0.357 g (89%). 1H
NMR (400 MHz, CDCl3): δ = 2.27 (s, 3 H), 2.29 (s, 3 H), 3.54 (d,
J = 6 Hz, 4 H), 5.10 (m, 4 H), 5.77 (m, 2 H), 6.92 (s, 1 H), 7.00 (s,
1 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 18.5, 21.1, 56.2,
116.9, 121.9, 126.5, 131.8, 132.5, 133.8, 135.5, 147.3 ppm. IR
IR (KBr): ν = 3065, 3046, 2968, 2833, 2873, 1598, 1505, 1364,
˜
1287, 1120, 1187, 988, 917, 806 cm–1. C13H18BrN (268.20): calcd.
C 58.22, H 6.76, N 5.22; found C 58.45, H 6.53, N 5.11.
1
4-(4-Nitrobenzyl)morpholine (13j): Yield: 0.408 g (92%). H NMR
(KBr): ν = 3071, 3000, 2923, 2851, 2813, 1503, 1418, 1264, 1212,
˜
(400 MHz, CDCl3): δ = 2.45 (m, 4 H), 3.58 (s, 2 H), 3.71 (m, 4 H),
1111, 990, 913, 812, 749 cm–1. C14H19N (201.31): calcd. C 83.53,
H 9.51, N 6.96; found C 83.68, H 9.49, N 7.03.
7.51 (m, 2 H), 7.51 (m, 2 H) ppm. 13C NMR (100 MHz, CDCl3):
δ = 53.7, 62.6, 67.0, 123.6, 129.6, 146.1, 147.3 ppm. IR (KBr): ν =
˜
3062, 3054, 2967, 2854, 2807, 1599, 1514, 1448, 1338, 1105, 1004,
858 cm–1. C11H14N2O3 (222.25): calcd. C 59.45, H 6.35, N 12.60;
found C 59.63, H 6.43, N 12.49.
Benzyl(butyl)phenylamine (1i): Yield: 0.445 g (93%). 1H NMR
(400 MHz, CDCl3): δ = 1.03 (t, J = 7.2 Hz, 3 H), 1.43 (m, 2 H),
1.73 (m, 2 H), 3.46 (t, J = 7.6 Hz, 2 H), 4.60 (s, 2 H), 6.72 (m, 3 H),
7.26 (m, 5 H), 7.35 (m, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ
= 14.2, 20.5, 29.4, 51.2, 54.6, 112.2, 116.0, 126.6, 126.8, 128.7,
Acknowledgments
129.3, 139.3, 148.7 ppm. IR (KBr): ν = 3063, 3028, 2958, 2932,
˜
2872, 1598, 1505, 1453, 1356, 1252, 1220, 1197, 988, 747, 693 cm–1.
C17H21N (239.36): calcd. C 85.31, H 8.84, N 5.85; found C 85.42,
H 8.63, N 5.95.
B. K. P. and C. B. S acknowledge the support of this research by
Department of Science & Technology (DST), New Delhi (SR/S1/
OC-15/2006) and the Council of Scientific and Industrial Research
(CSIR) (01(1946)/04/EMR-II) and V. K. thanks the Indian Insti-
tute of Technology (IIT). Thanks are due to CIF, IIT Guwahati
for providing NMR spectra and DST FIST for use of the XRD
facility.
Benzyl(4-bromophenyl)butylamine (6i): Yield: 0.585 g (92%). 1H
NMR (400 MHz, CDCl3): δ = 1.00 (t, J = 7.2 Hz, 3 H), 1.42 (m,
2 H), 1.68 (m, 2 H), 3.41 (t, J = 8.0 Hz, 2 H), 4.55 (s, 2 H), 6.56
(d, J = 8.4 Hz, 2 H), 7.26 (m, 5 H), 7.33 (d, J = 8.4 Hz, 2 H) ppm.
13C NMR (100 MHz, CDCl3): δ = 14.2, 20.5, 29.4, 51.4, 54.7,
107.9, 113.9, 126.5, 127.0, 128.8, 131.9, 138.6, 147.7 ppm. IR
[1] a) R. Breslow, Acc. Chem. Res. 1991, 24, 159; b) W. A. Herr-
mann, C. W. Kohlpaintner, Angew. Chem. Int. Ed. Engl. 1993,
32, 1524; c) C.-J. Li, Chem. Rev. 1993, 93, 2023; d) U. M.
(KBr): ν = 3060, 3027, 2961, 2923, 2868, 1593, 1497, 1451, 1363,
˜
1220, 1193, 1130, 1075, 930, 801, 724, 696 cm–1. C17H20BrN
1376
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Eur. J. Org. Chem. 2007, 1369–1377