2-Biphenylacetonitrile → 2-([1,1'-Biphenyl]-2-yl)ethanamine

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Reaction Steps

Combine 2-phenylphenylacetonitrile (4.69 g, 24.26 mmol) and diethyl ether (10 ml) and add dropwise to a cooled (−10°) solution of LiAlH4 (2.76 g, 72.81 mmol) in diethyl ether (100 ml). Warm to ambient temperature. After 2 hours, quench with saturated sodium sulfate (100 mL/mol). Filter to remove the precipitate, dry (Na2SO4) the filtrate, filter, and concentrate to residue. Chromatograph the residue on silica gel eluting with dichloromethane/2N NH3(methanol) (95/5) to give the title compound as a yellow oil. Prepare the HCl salt in diethyl ether: mp 197-199° C. MS (ACPI): m/e 198.1 (M+1). Analysis for C14H16ClN: Calcd: C, 71.94; H, 6.90; N, 5.99. found: C, 72.15; H, 6.84; N, 6.09.

Provenance & Evidence