Diisopropylamine → hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

Participants

Reaction Steps

Diisopropylamine (152 g) in tetrahydrofuran (150 ml) was added over 30 minutes to 15% butyl lithium in hexane (641 g, 1.50 mole) under nitrogen at 20°-25° C. with cooling and the mixture stirred 30 minutes at room temperature. N-methylcaprolactam (63.6 g) in tetrahydrofuran (60 ml) was added over 5 minutes below 25° C. with cooling, the mixture was stirred for one hour at room temperature and then o-chloroanisole (71.3 g) was added over 20 minutes keeping the temperature below 30° C. The reaction mixture was stirred for two hours, water (2. l.) was added, the product was extracted into ethyl acetate (2×1 l.), the extracts were combined, washed with 2 N hydrochloric acid (1. l.) and water (500 ml) and evaporated under reduced pressure to give 27.1 g oil.

Provenance & Evidence