Acetone → HCID 19734242, compound

Participants

Reaction Conditions

Reaction Steps

0.82 g of borane-dimethylamine complex was added to a stirred solution of 3-aminomethyl-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole hydrate (see Example 1C for preparation) in 80 ml of tetrahydrofuran. The solution was heated under reflux for 1 hour and subsequently, at a temperature of 45° C., 10 ml of acetone were added dropwise. The reaction mixture was stirred at a temperature of 60° C. for 2.5 hours. To work up the reaction mixture it was subsequently evaporated to dryness, and the residue was dissolved in a mixture of water and dichloromethane. The dichloromethane phase was separated, and the aqueous phase was extracted three more times with 50 ml portions of a 9:1 dichloromethane/methanol mixture. The organic phases were combined and evaporated to dryness. The crude product which remained as residue was purified by chromatography under slightly elevated pressure (=flash chromatography) on silica gel using methanol/ethyl acetate 4:1 as eluent. The title compound was obtained as an oil.

Provenance & Evidence