Hydrochloric Acid → HCID 13324722, compound

Participants

Reaction Steps

A solution of 7.1 g (32.3 mmole) of 3-(1-indolinyl)benzonitrile of Example 3a in 44 ml THF was added dropwise over 30 minutes to an ice cold solution of 129 ml (129 mmole, 4 equivalents) of 1 M BH3.THF complex under nitrogen. After heating at reflux for 1 hour, the reaction mixture was cooled to 0°-5° C. and treated dropwise with 50 ml concentrated HCl. The resulting suspension was heated at reflux for 1 hour, permitted to stand at room temperature overnight (about 16 hours) and then made basic using 50% NaOH (60 ml). The reaction mixture was partitioned between water--CH2Cl2 (300 ml each) and the organic phase was washed with brine (300 ml), dried over MgSO4 and concentrated to give 8.9 g of crude free base. Conversion as in Example 1 to the HCl salt (ethanol/ethereal HCl) and recrystallization from hot acetonitrile-methanol afforded 2.86 g (34% overall) of 3-(1-indolinyl)benzenemethanamine hydrochloride, m.p. 170.5°-173.5° C.

Provenance & Evidence