Acetic Acid → HCID 22414428, compound

Participants

Reaction Steps

A stirred solution of 3.05 g of 2-amino-4-chloro-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine, 11.63 g of triethyl orthopropionate and 3.7 ml of glacial acetic acid, was refluxed for 8 hr and then concentrated at 80° C. The residue was washed with 10% hydrochloric acid, and the aqueous phase was washed with ether, basified with 10% sodium hydroxide solution and extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated. Purification was accomplished by preparative HPLC (Water's Associates Prep LC/System 500A, silica gel, eluted with methanol, flow rate of 200 ml/min, GOW-MAC Model 80-800 UV detector). The appropriate fractions were combined and concentrated to afford a solid. The solid was dissolved in ether and filtered. The filtrate was concentrated and the residue was triturated with ether to give 1.2 g of product, mp 94°-96° C.

Provenance & Evidence