Aluminium lithium hydride → 1-(2-(1-Methylpyrrolidin-2-yl)ethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-amine

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Reaction Steps

A solution of compound 3 (825 mg, 2.87 mmol) in anhydrous THF (15 mL) was cooled to 0° C. and treated drop wise with LiAlH4 (1.0 M in THF, 11.5 mL, 11.5 mmol). The reaction mixture was warmed to room temperature and stirred overnight (23 h). The reaction mixture was cooled to 0° C. and quenched with H2O (0.4 mL), 2 N NaOH (0.4 mL), and additional H2O (0.4 mL) and stirred for 30 minutes upon, which a white precipitate formed. The solid was filtered off and washed with CH2Cl2 (2×50 mL) and the filtrate concentrated. The crude product was purified by column chromatography (2N NH3 in MeOH:CH2Cl2, 5:95) to give compound 4 (590 mg, 75%) as a thick brown syrup.

Provenance & Evidence