Benzylamine → HCID 20029845, compound

Participants

Reaction Steps

A mixture of 1,6-dibromohexane (73.84 g) 4-(N,N-dimethylamino)benzeneethanol (10 g), 50% w/v sodium hydroxide solution (200 ml) and TAB (3.4 g) was virgorously stirred at room temperature for 72 h, diluted with water (500 ml) and extracted with ER (2×100 ml). The dried extracts were evaporated to give a yellow oil which was purified by FCC eluting with H then H-EA (9:1) to give 4-[2-[(6-bromohexyl)oxy]ethyl]-N,N-dimethylbenzeneamine as a yellow oil. The benzeneamine (15 g) was added to benzylamine (45 ml) with stirring at 140° under nitrogen and stirring continued for 2 h. The benzylamine was removed in vacuo at 90°, the solution was partitioned between sodium bicarbonate (150 ml) and EA (2×100 ml) and the combined organic layers dried and concentrated to give a product which was purified by FCC eluting with ER-H (1:1→ER) to give the title compound as a yellow oil (11.1 g) t.l.c. (T-ET-A 95:4:1) Rf 0.62.

Provenance & Evidence