Benzaldehyde → HCID 54398611, compound

Participants

Reaction Steps

A mixture of (R)-8-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (5.8 g; contaminated with ammonium bromide), benzaldehyde (5.3 ml), acetic acid (0.15 ml), 10% palladium on carbon (50% wet; 1.1 g), and ethanol (260 ml) was stirred under hydrogen for 1 hour, and then an additional portion of benzaldehyde (5.3 ml) was added. After aging for 0.5 hour, hydrogen was introduced to the reaction mixture and stirring was continued for an additional 3 hours. To the reaction mixture was added an additional portion of acetic acid (0.15 ml), and the mixture was stirred under 1 atm of hydrogen for an additional 1 hour. The catalyst was filtered off, and washed with ethanol. Removal of the solvent in vacuo afforded the residue, which was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; chloroform, then 100:1 to 50:1 to 10:1 chloroform-methanol) to give (R)-8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (6.6 g). Physical data are shown for the hydrochloride of the product, which was recrystallized from 3:1 diisopropyl ether-ethanol.

Provenance & Evidence