Potassium Carbonate → HCID 59837351, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[4-(3-chloro-propoxy)-phenyl]-tetrahydropyran-4-carbonitrile and 4-[4-(3-bromo-propoxy)-phenyl]-tetrahydropyran-4-carbonitrile (7.5 g, 27 mmol), K2CO3 (9.6 g, 70 mmol) and azetidine hydrochloride (4.0 g, 43 mmol) in acetonitrile (80 mL) was heated at 40° C. for 18 hours. The mixture was concentrated in vacuo then partitioned between water (150 mL) and ethyl acetate (150 mL). The organic layer was extracted with 2M HCl solution (2×100 mL) and the combined acid layers basified with 40% potassium hydroxide solution, then extracted with DCM (2×150 mL). The DCM layers were combined, dried over sodium sulphate, filtered and concentrated under reduced pressure to give the title compound (1.1 g, 57%) as a clear, viscous oil. 1H NMR (400 MHz, DMSO) δ 1.80 (quintet, 2H), 2.00-2.14 (m, 6H), 2.58 (t, 2H), 3.20 (t, 4H), 3.88 (m, 2H), 4.00-4.11 (m, 4H), 6.90 (d, 2H), 7.38 (d, 2H). LRMS (APCI+) m/z 301 (MH)+.

Provenance & Evidence