Aluminium lithium hydride → [3-(1H-Indol-7-yl)-3-phenyl-propyl]-methyl-amine

Participants

Reaction Steps

To a stirring solution of 3-(1H-indol-7-yl)-N-methyl-3-phenyl-propionamide XIX (296 mg, 1.06 mmol) in THF (8 ml) was added a suspension of LiAlH4 (165 mg, 4.24 mmol) in THF (6 ml) at room temperature. The mixture was refluxed for 5 hours, cooled to room temperature, and quenched by slow addition of freshly ground Na2SO4.10H2O (4 g). The resulting mixture was stirred at room temperature for 45 minutes, and the solid was filtered and washed with EtOAc. The filtrate was concentrated and purified via flash chromatography (DCM/MeOH) affording [3-(1H-Indol-7-yl)-3-phenyl-propyl]-methyl-amine XX (182 mg, 65% yield). The free amine (100 mg) was dissolved in Et2O (15 ml) and cooled to 0° C. To the resulting solution was added HCl (1 M in Et2O, 568 μl), and the precipitate was filtered and dried in vacuo to afford the hydrochloride salt. (62 mg, 36% yield). MS (M+H)=265.

Provenance & Evidence