Diisopropylamine → HCID 12665522, compound

Participants

Reaction Steps

A solution of hexahydro-1-phenylmethyl-2H-azepin-2-one (5.68 g) in dry THF was added at -10° C. to lithium diisopropylamide (0.032 mm) prepared from diisopropylamine (4.4 ml) and butyl lithium (22.9 ml of 1.4 M solution in hexane). The mixture was stirred for 30 minutes and then treated with a solution of 3-methoxy-2-cyclohexenone (2.53 g) in THF. After 5 hours at ambient temperature the mixture was poured onto ice-cold concentrated hydrochloric acid (100 ml). After vigorously stirring for 12 hours the solution was shaken with several portions of chloroform. The combined chloroform layers were evaporated to give an orange oil. This was refluxed with cupric bromide (8.95 g) and lithium bromide (1.74 g; 0.02 m) in acetonitrile for 1 hour. Removal of the solvent left a black oil that was triturated with excess 2 N sodium hydroxide solution. The filtrate, after removal of the orange precipitate, was extracted with methylene chloride. The organic layer was acidified (conc.HCl) and the white suspension shaken with several portions of chloroform and were evaporated to leave a dark red oil (1.2 g) that crystallised from ethyl acetate to give the title compound (0.35 g) m.p. 160°-166° C.

Provenance & Evidence