Hydrochloric Acid → 7-Amino-5-(4-methoxybenzyl)-5H-dibenzo[b,d]azepin-6(7H)-one hydrochloride

Participants

Reaction Conditions

Reaction Steps

Aqueous HCl 2N (20.8 mL) was added to a solution of 5-(4-methoxy-benzyl)-5H-dibenzo[b,d]azepine-6,7-dione 7-oxime (8.3 g) in methanol (83.0 mL). Pd/C (10% weight, 540 mg) was added to the reaction mixture and the system was stirred under 10 bar H2 at 50° C. for 2 days. After exchanging H2 for Ar, the reaction mixture was filtered, concentrated under reduced pressure and dried under high vacuum yielding 7-amino-5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one hydrochloride (8.7 g, quant.) as a light yellow powder. This powder was suspended in acetonitrile (43 mL) and stirred 2 hours at room temperature. The precipitate was filtered off, washed with acetonitrile and dried under reduced pressure yielding 7-amino-5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one hydrochloride (8.3 g, 96%) as an off-white powder.

Provenance & Evidence