Chloromethyl pivalate → 2-[(Diphenylmethylene)amino]-2-quinolin-4-ylethyl pivalate

Participants

Reaction Conditions

Reaction Steps

A Stirred mixture of 1-quinolin-4-ylmethanamine (142 mg, 0.90 mmol, CHEMBRIDGE) and benzophenone imine (163 mg, 0.90 mmol) was heated at 50° C. for 2 hours. The resultant product was dissolved in dichloromethane (4 ml) and added to a solution of chloromethyl pivalate (136 mg, 0.90 mmol) and tetrabutylammonium bromide (150 mg, 0.465 mmol). 50% NaOHaq (0.9 ml) was added to the reaction mixture at 0° C. After the mixture was stirred at 0° C. for 1 hour, the reaction was diluted with dichloromethane (30 ml) and water (30 ml). The organic layer was separated, dried over Na2SO4, concentrated in vacuo and purified through silica gel column chromatography eluting with Hexane/EtOAc (3:1 to 2:1) to furnish the title compound (142 mg, 36% yield) as colorless oil. MS (ESI) m/z 437 (M+H)+.

Provenance & Evidence