Phenylacetyl chloride → HCID 67915864, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.45 cc) and then phenylacetyl chloride (0.49 g) are added to a solution, cooled to +4° C., of 7,7-bis(3-chlorophenyl)perhydro-4-isoindolone hydrochloride (1.06 g) in dichloromethane (20 cc). The reaction mixture is stirred for 2 hours at 25° C. and then washed with water (3×30 cc) and saturated sodium chloride solution (3×30 cc). The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.04-0.063 mm, diameter 2.2 cm, height 23 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (55:45) and collecting 15-cc fractions. Fractions 7 to 18 are concentrated to dryness under reduced pressure (2.7 kPa) and the residue is crystallized in acetonitrile. The crystals are drained, washed with isopropyl ether and dried. (3aRS,7aRS)-7,7-Bis(3 -chlorophenyl)-2-(phenylacetyl)perhydro-4-isoindolone (0.21 g) is obtained. M.p. 160° C.

Provenance & Evidence