Hydrochloric Acid → HCID 53840445, compound

Participants

Reaction Steps

To a solution of 1-[(5-amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-N-(diphenylmethyl)-4-piperidinecarboxamide (1.3 g) in tetrahydrofuran (20 mL) was added 17 mL of 1 M borane tetrahydrofuran complex solution in tetrahydrofuran with ice-cooling and the mixture was refluxed under nitrogen gas for 23 hours. After this reaction mixture was cooled with ice, 12 mL of 5N-hydrochloric acid was added dropwise and the mixture was concentrated under reduced pressure. The residue was neutralized with sodium hydrogen carbonate and extracted with 2 portions of ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethanol=10:1) to give 0.89 g of 1-[(5-amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-N-(diphenylmethyl)-4-piperidinemethylamine. Yield 68%. This product was dissolved in methanol and a stoichiometric excess of 10% HCl solution in methanol was added dropwise. The mixture was concentrated under reduced pressure to provide the title compound.

Provenance & Evidence