Hydrochloric Acid → HCID 19762431, compound

Participants

Reaction Steps

3-(4-Quinolinylmethoxy)benzoic acid methyl ester (10.25 g, 35 mmol) and 2.5N NaOH (aq) (70 ml, 175 mmol) were refluxed for 2 hours in MeOH (300 mL). Neutralization with conc. HCl (14.5 mL, 175 mmol) and filtration afforded 9.5 g (34 mmol, 97%) of air-dried 3-(4-quinolinylmethoxy)benzoic acid as a white solid. The free acid (9.0 g, 32 mmol) was refluxed in excess thionyl chloride (50 mL, neat) for 10 minutes. Dichloroethane and ether were added and the resulting precipitate filtered to afford 3-(4-quinolinylmethoxy)benzoyl chloride hydrochloride as a cream colored solid. The acid chloride (3.34 g, 10 mmol), resuspended in methylene chloride, was treated with 4-amino-1-benzylpiperidine (3.80 g, 20 mmol) and, after 0.5 hours, extracted with 1N NaOH (aq) and water. Evaporation of the organic phase, crystallization of the residue from methylene chloride-ether-hexane, and purification by flash column chromatography on silica gel afforded, after recrystallization from acetonitrile, 3.1 g (6.9 mmol, 69% yield) of the product as a pale yellow solid, m.p. 160°-163° C.

Provenance & Evidence