Ammonium Chloride → 2-(3,5-Dichloropyridine-4-yl)-1-(7-methoxy-spiro[1,3-benzodioxole-2,4'-piperidine]-4-yl)ethanone

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Reaction Steps

A solution of methyl 7-methoxy-spiro[1,3-benzodioxole-2,4′-piperidine]-4-carboxylate (75 mg, 0.268 mol) and 3,5-dichloro-4-picoline (65 mg, 0.40 mmol) in tetrahydrofuran (2.5 mL) was cooled to 0° C. A 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (0.80 mL, 0.80 mmol) was added and the reaction mixture was allowed to reach room temperature overnight. Saturated aqueous NH4Cl (10 mL) was added. The aqueous phase was extracted with dichloromethane (3×10 mL). The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure. Standard HPLC purification afforded compound 105 (58 mg, 53%). 1H NMR (DMSO) δ 8.66 (s, 2H), 7.38-7.36 (m, 1H), 6.83-6.80 (m, 1H), 4.62 (s, 2H), 3.91 (s, 3H), 3.02-2.91 (m, 4H), 2.12-1.93 (m, 4H).

Provenance & Evidence