Hydrochloric Acid → HCID 57699405, compound

Participants

Reaction Conditions

Reaction Steps

Synthesized according to General procedure 35. To a solution of (R)-1-((S)-3-(3,5-dichlorophenyl)piperidin-1-yl)-2-methoxy-2-phenylethanone (98 mg, 0.26 mmol) in anhydrous THF (9 mL) under nitrogen at 0° C. was added Super-hydride (1.0 M in THF, 1.63 mL, 1.63 mmol) dropwise. The solution was stirred at 0° C. for 2 h, and then poured into 2M aqueous HCl (3 mL). The aqueous phase was washed twice with Et2O (2×3 ml), then basified by addition of NH4OH at 0° C. The product was extracted with DCM (3×3 ml), the organic phases were combined, dried over sodium sulfate, filtered, then concentrated under reduced pressure, providing 3-(3,5-dichlorophenyl)piperidine (59 mg, 67%) which was arbitrarily assigned the (S)-configuration, as a pale yellow oil. This material was used without further purification. 1H-NMR (400 MHz, CDCl3) δ 7.22 (s, 1H), 7.20 (t, J=1.8 Hz, 1H), 7.09 (d, J=1.8 Hz, 2H), 3.17-3.05 (m, 2H), 2.65-2.57 (m, 3H), 2.01-1.96 (m, 1H), 1.81-1.77 (m, 1H), 1.60-1.53 (m, 2H), 1.60-1.53 (m, 2H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=230.3; tR=1.10 min.

Provenance & Evidence