p-Toluenesulfonic acid → HCID 19762423, compound

Participants

Reaction Steps

A mixture of 4-(4-quinolinylmethoxy)benzaldehyde (2.63 g, 10 mmol), 4-amino-1-benzylpiperidine (2.5 g, 13.1 mmol), and 4-toluenesulfonic acid (0.38 g, 2 mmol) was refluxed in toluene (500 mL) for 15 hours with azeotropic removal of water. The solvent was removed in vacuo, and the residue redissolved in MeOH. The stirred solution was treated with solid sodium borohydride (1 g, 26.5 mmol) at room temperature for 1 hour. The solvent was removed in vacuo, the residue redissolved in methylene chloride, and extracted with 1N NaOH (aq) (2×100 mL), and water(2×100 mL). The dried (MgSO4) organic phase was evaporated in vacuo and treated with etheral-hydrogen chloride(g) in methanol to afford the title compound (4.6 g, 9.0 mmol, 90% yield) as the dihydrochloride salt. The dihydrochloride salt was converted to the free base with 1N NaOH (aq) and extracted with methylene chloride. The organic phase was washed with water (2×75 mL), dried (MgSO4), evaporated in vacuo, and the residue crystallized from ether-hexane to afford, after drying in vacuo (6 hours at 45° C.) overnight, the free base of the title compound, m.p. 72°-75° C.

Provenance & Evidence