Water → N-[2-(3,4-Difluorophenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide

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Reaction Conditions

Reaction Steps

To a stirred cooled (0° C.) mixture of 3-(3,4-difluorophenyl)-N-methyl-4-amino-1-butanol (0.917 g, 4.26 mmol) in DCM (35 mL) and 1N NaOH (10 mL) was added dropwise a solution of 5,6,7,8-tetrahydro-1-naphthalenecarbonyl chloride (0.829 g, 4.26 mmol) in DCM (20 mL). The mixture was stirred at 0° C. for 2.5 h, additional H2O and DCM were added and the mixture was extracted with DCM (2×20 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. Purification by chromatography (0%, 50%, 100% EtOAc in Et2O) provided the title compound (1.25 g, 79%) as a solid. MS m/z 374 (M+H).

Provenance & Evidence