Oxalyl chloride → N-(3,3-Diethoxypropyl)-N-phenethyl-3-phenethyloxy-propanamide

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Reaction Steps

Oxalyl chloride (0.078 g) was added dropwise to a solution of 3-phenethyloxypropanoic acid (0.10 g) in dichloromethane (10 mL), dimethyl formamide (1 drop) was added and stirring continued at room temperature for 1 hour. The mixture was subsequently concentrated, redissolved in dichloromethane (10 mL) and added dropwise to a solution of the crude 3,3-diethoxy-N-phenethyl-propan-1-amine, prepared as described in Example 8a) (0.33 g), and diisopropylethylamine (0.37 g) in dichloromethane (10 mL). The resulting mixture was stirred at room temperature for 1 hour, diluted (dichloromethane, 50 mL), washed with water (2×20 mL), brine (20 mL), dried over magnesium sulfate and concentrated to give a crude product (0.32 g). The latter was purified by passing through a plug of SCX resin, eluting with methanol (100 mL) to give the sub-titled compound as a clear oil (0.127 g).

Provenance & Evidence