DOI: 10.1055/s-00000083

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 

Download Bibliographical Data

Access: