Aluminium lithium hydride → HCID 60036800, compound

Participants

Reaction Steps

Intermediate XXXI, e.g. tert-butyl 4-[amino(phenyl)methyl]piperidine-1-carboxylate (1.0 g, 3.44 mmol) was dissolved in dry THF (50 mL). LiAlH4 (261 mg, 6.89 mmol) was added in portions. The reaction was heated under reflux overnight. As the reaction was completed, it was quenched with dropwise addition of water (5 mL), followed by NaOH 1N (5 mL) and H2O (5 mL). The suspension thus obtained was extracted with ethyl acetate, dried over MgSO4 and evaporated, affording the crude product. It was further purified by flash chromatography (DCM/MeOH 20:1 with 2% NH4OH) to give the tertiary amine XXXII, e.g., 1-(1-methylpiperidin-4-yl)-1-phenylmethanamine (444.6 mg, 63% yield).

Provenance & Evidence