Triethylamine → N-[2-(4-chlorophenyl)-4-oxobutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide

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Reaction Conditions

Reaction Steps

To a stirred cooled (−78° C.) solution of oxalyl chloride (0.39 mL, 4.47 mmol) in DCM (10 mL) was added DMSO (0.64 mL, 9.00 mmol) in DCM (5 mL) dropwise. The solution was stirred at −78 ° C. for 5 min and a solution of N-[2-(4-chlorophenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide (1.11 g, 2.98 mmol) in DCM (6.0 mL) and DMSO (3.4 mL) was added dropwise. The solution was stirred at −78 ° C. for 15 min and triethylamine (2.50 mL, 17.9 mmol) was added. Stirring was continued at −78 ° C. for 30 min and then at room temperature for 2 h. 1N NCI (75 mL) and DCM (75 mL) were added, the layers separated, and the organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by chromatography (silica gel; 50% Et2O/DCM) provided the title compound (1.10 g, 95%) as a tacky solid. MS rm/z 370 (M+H).

Provenance & Evidence