Phenylacetyl chloride → HCID 18433031, compound

Participants

Reaction Steps

To a room temperature solution of (RS)-1-amino-3-(2-phenyl-quinolin-4-ylamino)-propan-2-ol (0.293 g, 1 mmol) and triethylamine (0.42 ml,3 mmol) in dioxane (6 ml) was added a solution of phenylacetylchloride (0.198 ml, 1.5 mmol) in dioxane (1 ml). After stirring for 3 hours at room temperature, the reaction mixture was quenched with H2O and 1N NaOH. The aqueous phase was extracted with CH2Cl2 (5×10 ml). The combined organic phases were dried over Na2SO4, concentrated and chromatographed over silica gel (CH2Cl2—MeOH, 19:1 then 9:1) to provide a yellow oil which was dissolved in MeOH. HCl-Et2O was added to provide (RS)-N-[2-hydroxy-3-(2-phenyl-quinolin-4-ylamino)-propyl]-2-phenyl-acetamide hydrochloride (0.113 g, 25%) as a light yellow foam, MS: m/e=412.3 (M+H+).

Provenance & Evidence