Aluminium lithium hydride → HCID 17747058, compound

To a 0° C. stirring suspension of LiAlH4 (0.062 g, 1.69 mmol) in THF (12 ml) under N2 was added a solution [3-(1H-indol-4-yl)-3-phenyl-propyl]-carbamic acid methylester (V) (0.46 g, 1.5 mmol) in THF (7 ml). The resulting mixture was stirred for 15 minutes at room temperature, after which a suspension of LiAlH4 (0.11 g, 3 mmol) in THF (5 ml) was added. The reaction mixture was then refluxed for about 2.5 hours, cooled to about 0° C., and quenched by addition of freshly ground Na2SO4.10H2O (8 g). The resulting mixture was stirred vigorously for about 30 minutes and filtered with the aid of EtOAc. The filtrate was concentrate and purified via flash chromatography (DCM/MeOH/NH4OH) affording [3-(1H-Indol-4-yl)-3-phenyl-propyl]-methyl-amine (0.30 g, 75% yield). To a 0° C. stirring solution of the above amine (0.24 g, 0.90 mmol) in Et2O (10 ml) was added HCl (2 M in Et2O, 0.5 ml, 1.0 mmol). The resulting precipitate was filtered and washed with water and Et2O. The white solid was dried in vacuo affording [3-(1H-indol-4-yl)-3-phenyl-propyl]-methyl-amine (VI) as a hydrochloride salt, (0.21 g, 78% yield). MS (M+H)=265.