Acetic Acid → HCID 22414416, compound

Participants

Reaction Steps

A solution of 3.95 g of 2-amino-N-methyl-α-(2-methyl-3-thienyl)benzeneethanamine, 5 ml of glacial acetic acid and 17.0 g of triethylorthopropionate was refluxed for 8 hours (under a nitrogen atmosphere). The solution was concentrated in vacuo at 80° C. and the residual oil dissolved in diethyl ether (50 ml) and acidified with 10% hydrochloric acid solution. The aqueous phase was washed with diethyl ether (50 ml), basified, and extracted with dichloromethane (2×100 ml). The combined organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The resultant oil was purified by preparative HPLC (Water's Associates Prep LC/System 500, silica gel, elution with methanol followed by 2% triethylamine in methanol). Concentration of the appropriate fractions afforded 2.26 g of 4,5-dihydro-2-ethyl-3-methyl-4-(2-methyl-3-thienyl)-3H-1,3-benzediazepine as an oil. Trituration with hexane afforded a solid which was combined with product obtained from previous run to afford the analytical sample, mp 82°-83.5° C.

Provenance & Evidence