4-Piperidinecarboxamide → 1-(5-(4-Fluorophenyl)thieno[3,2-b]pyridin-7-yl)-4-piperidinecarboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-chloro-5-(4-fluorophenyl)thieno[3,2-b]pyridine (68 mg, 0.26 mmole), isonipecotamide (66 mg, 0.52 mmole), and sodium acetate (21 mg, 0.26) in 1-methyl-2-pyrrolidone (3 mL) is stirred and heated in an oil bath at 160° C. for 4 hours. The reaction mixture is then cooled and diluted with EtAc (15 mL), transferred to a separatory funnel, and washed with water (3×15 mL). The organic layer is dried over sodium sulfate and concentrated. The residue is recrystalized with ethyl acetate to give 1-(5-(4-fluorophenyl)thieno[3,2-b]pyridin-7-yl)-4-piperidinecarboxamide (55 mg, 60% yield) as a white solid. This material is dissolved in ethyl acetate and HCl saturated ethyl acetate (2 mL) is added. The solution is concentrated to afford the HCl salt as a greasy oil. 1-(5-phenylthieno[3,2-b]pyridin-7-yl)-4-piperidinecarboxamide hydrochloride (compound 3) is precipitated out of an ether solution, collected by filtration, washed with ether, and dried in vacuo to afford the final product. m.p. 303-305° C. (dec).

Provenance & Evidence