Hydrochloric Acid → HCID 13324746, compound

Participants

Reaction Steps

A solution of 15.53 g (45.35 mmole) of 3-(1-indolinyl)-N-phenylacetylbenzenemethanamine of Example 12 in 65 ml distilled THF was added dropwise over 30 minutes to an ice-salt cooled, rapidly stirred slurry of 10.44 g (275.1 mmole, 6.07 equivalents) LiAlH4 in 275 ml distilled THF under nitrogen. After warming to room temperature and stirring for 2 hours, the reaction mixture was heated under reflux for 19 hours and then quenched at 0° C. with 20 ml ice water-THF (1:1), 10 ml 10% NaOH, and 30 ml water. The salts were filtered, washed with CHCl3 and the filtrate was concentrated. The residue was dissolved in CHCl3, washed with brine, dried over Na2SO4, and concentrated to give 11.70 g (78.6%) of crude free base. Conversion to the HCl salt (ether/ethereal HCl) using the procedure of Example 1 gave 11.43 g (69.1%). Recrystallization from hot absolute ethanol gave 2.88 g (17.4% overall) of 3-(1-indolinyl)-N-(2-phenylethyl)benzenemethanamine hydrochloride, m.p. 188°-190° C.

Provenance & Evidence