Triethylamine → HCID 66822304, compound

Participants

Reaction Steps

Oxalyl chloride (0.19 g, 1.49 mmol) was added to a stirred solution of cyanoacetic acid (0.107 g, 1.25 mmol) in a mixture of dichloromethane (5 mL) and 2 drops of dimethylformamide under nitrogen at ice bath temperature. After 2 hours the solution was added in one portion to a solution of 1-(4-(2-methoxyethoxy)phenyl)propan-1-amine (0.25 g, 1.2 mmol) and triethylamine (0.13 g, 1.3 mmol) in tetrahydrofuran/dichloromethane 1:1 (4 mL) at 0-5° C., and the mixture was allowed to warm slowly to room temperature. After 4 hours 80 mL of water was added and after half an hour more (30 mL) dichloromethane was added. The layers were separated and the aqueous layer extracted with additional dichloromethane. The combined extracts were washed with 1N aq sodium bicarbonate, and then sat brine, and dried over magnesium sulfate. The solvent was removed in vacuo, leaving a cloudy amber syrup which was dissolved in EtOAc/Hxa 1:1 and filtered through a short column of silica gel under pressure. The effluent was concentrated in vacuo to afford 0.24 g of the product as a cloudy pale amber syrup, sufficiently pure for the next step.

Provenance & Evidence