Ammonia → HCID 17955453, compound

Participants

Reaction Steps

A solution of 9-chloromethyl anthracene (278 mgr, 1.22 mmoles) in dichloromethane (1.5 ml) was bubbled with gaseous ammonia for 10 minutes. More dichloromethane was added, the reaction vessel was tightly closed and the reaction mixture was stirred for two days, at room temperature. Concentration in vacuo and purification of the crude product by flash chromatography afforded 30 mgr (14%) of N,N-di-(9-anthrylmethyl)-amine as yellow solid. 1H NMR (250 MHz, CDCl3): δ 8.48 (2H, s), 8.25-8.10 (4H, m), 8.09-7.80 (4H, m), 7.55-7.25 (8H, m), 4.95 (4H, s), 1.98 (NH, broad) ppm; 13C NMR (62.5 MHz, CDCl3): δ 131.8, 131.3, 130.4, 129.3, 128.4, 126.2, 125.1, 124.2, 45.6 ppm; FTIR: 3317, 3052, 2919, 2846, 1938, 1726, 1620, 1448, 1096, 1030, 891, 738 cm−1. HRMS (MALDI) calcd for C30H23N [M+H+] 398.1903, found 398.1917.

Provenance & Evidence