Hydrochloric Acid → HCID 59850191, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-[4-(5,6-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-3,6-dihydro-1(2H)-pyridinyl]tetrahydro-2H-pyran-4-carbonitrile (D101) (0.32 mmol, 113 mg) in tetrahydrofuran (10 mL) was treated at room temperature under argon with methyl magnesium bromide (0.96 mmol, 0.32 mL of 3M solution in tetrahydrofuran, 3 eq) dropwise over 2 min. The mixture became a solution and was stirred for 45 min. Then 6 more equivalents of methyl magnesium bromide were added and stirred for 3 h. The mixture was cooled down to 0° C. and 1M aqueous ammonium chloride solution was added until everything was solubilised. Tetrahydrofuran was removed under reduced pressure and the mixture was diluted with water and extracted 3 times with ethyl acetate. The organics were combined, dried and concentrated to give a white solid (0.26 mmol, 89 mg, 81% crude yield). This solid was dissolved in 3 mL of dichloromethane and treated with 1 mL 1M ethereal hydrogen chloride. A yellow gum crashed out of the mixture. More ether was added and the gum turned into crystals upon trituration. The crystals were filtered off and dried to give the title compound as its hydrochloride salt (0.2 mmol, 75 mg, 62% yield) still containing hydrogenated compound (no double C═C bond in the piperidine core). M+H 342.1, 344.1, M−H 340.3.

Provenance & Evidence