Synlett
References
Analytical data for selected products:
()-1-[3-(5-Azido-pentyl)phenyl]ethylamine
(): H NMR (400 MHz, CDCl): δ = 1.41
(tt, = 7.2,
7.2 Hz, 2 H, NCHCHC), 1.44 (d, = 6.4 Hz,
3 H, CHC), 1.62
(tt, = 7.6,
7.2 Hz, 2 H, CCH-Ar),
1.63 (tt, = 7.2,
7.2 Hz, 2 H, CCHN), 2.60
(t, = 7.6
Hz, 2 H, C-Ar),
3.25 (t, = 7.2 Hz,
2 H, NC),
4.12 (q, = 6.4
Hz, 2 H, CCH),
4.52 (br s, 2 H, NH), 7.08 (d, = 7.2 Hz,
1 H, Ar-), 7.14
(s, 1 H, Ar-), 7.15 (d, = 7.2 Hz,
1 H, Ar-), 7.24
(dd, = 7.2,
7.2 Hz, 1 H, Ar-)
ppm. C NMR (100 MHz, CDCl): δ = 23.4 (CHH), 26.4 (NCHCHH), 28.7 (NCHH), 30.9 (HCH-Ar),
35.7 (H-Ar), 51.3 (NH), 51.4 (H), 123.5
(-Ar-H), 126.2 (-Ar-H), 127.8 (-Ar-H), 128.7 (-Ar-H), 142.9 [-Ar(CH)],
143.5 [-Ar(CH)] ppm. FTIR
(film on KBr): 2936, 2860, 2097, 1678, 1542, 1490, 1452, 1385, 1256,
1203, 1136, 897, 835, 799, 721, 706, 558, 461 cm;
MS (FAB, matrix: NBA): / (%) = 233(100) [M + H],
205(6) [M - N];
HRMS: / calcd:
233.1766; found: 233.1769. ()-1-[3-(5-Azidopent-1-enyl)phenyl]- ethylamine
(): H NMR (400 MHz,
CDCl): δ = 1.38 (d, = 6.8
Hz, 3 H, NCHC),
1.87 (tt, = 6.8,
6.8 Hz, 2 H, CHCCH),
2.44 (t, = 6.8
Hz, 2 H, CC≡C),
3.91 (t, = 6.8
Hz, 2 H, NC),
4.04 (q, = 6.8
Hz, 1 H, CCH), 5.62
(br s, 2 H, NH), 7.18 (dd, = 4.0,
3.6 Hz, 1 H, Ar-), 7.18
(d, = 4.0
Hz, 1 H, Ar-),
7.20-7.28 (m, 1 H, Ar-), 7.31 (s, 1 H, Ar-) ppm. C
NMR (100 MHz, CDCl): δ = 16.7 (HC≡C), 21.9 (CHH), 27.8 (NH), 50.2 (CHHCH), 51.2 (H), 81.1 (C≡-Ar),
88.8 (≡C-Ar), 124.2 [-Ar(C≡C)],
125.8 (-Ar-H), 128.9 (-Ar-H), 129.5 (-Ar-H), 131.4 (-Ar-H), 141.3 [-Ar(CH)] ppm. FTIR
(film on KBr): 2932 (m), 2099, 1678, 1602, 1483, 1430, 1367, 1293,
1256, 1202, 1134, 897, 834, 798, 721, 700, 476; MS (FAB, matrix: NBA): / (%) = 229(50)[M + H],
212(100) [M - NH];
HRMS: / calcd:
229.1453; found: 229.1449. 2-[2-(2-Azidoethoxy)ethoxy]ethylamine (): Analytical data are consistent with
those reported by: Klein E, DeBonis S, Thiede B, Skoufias DA, Kozielski F, Lebeau L,
Bioorg. Med. Chem.. 2007; 6474
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