HCID 86639103, compound → HCID 66811513, compound

Participants

Reaction Steps

To a solution of 2-[(benzylamino)carbonyl]-3-phenylpiperidinium trifluoroacetate (604 mg, 1.48 mmol) in THF (2 ml) at 0° C. was added 2M borane-THF complex in THF (7.5 ml, 14.8 mmol). The reaction was allowed to stir for 18 h. Additional 2M borane-THF complex in THF (1.5 ml, 2.96 mmol) was added to the reaction mixture and allowed to stir for an additional 24 h. The reaction was quenched with methanol, concentrated in vacuo, and concentrated again from 4M HCl in dioxane. The crude product was purified via reverse phase preparative HPLC to yield 1-phenyl-N-[(3-phenylpiperidin-2-yl)methyl]methanamine (20%). 1H NMR (400 MHz, CD3OD) δ 7.42-7.28 (m, 10H), 4.05 (m, 2H), 3.82 (m, 1H), 3.58 (d, J=10.9 Hz, 0.4H), 3.38 (m, 2H), 3.21 (m, 0.6H), 2.96 (m, 1H), 2.20 (m, 1H), 1.97 (m, 3H).

Provenance & Evidence