Hydrochloric Acid → HCID 69128659, compound

Participants

Reaction Steps

A solution of 6-methyl-2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile (D94) (μmol, 256 mg) in dichloromethane (10 mL) was treated with tetrahydro-4H-pyran-4-one (10 mmol, 1.0 g, 10 eq) and triethylamine (3 mmol, 303.6 mg, 3 eq) at room temperature under argon, then sodium triacetoxyborohydride (10 mmol, 2.12 g, 10 eq) was added and the mixture was allowed to stir for 6.5 h and to stand overnight. The mixture was diluted with dichloromethane and treated with aqueous sodium hydroxide so that the pH was maintained around 12. The aqueous phase was extracted with dichloromethane and the organics were combined, washed with an aqueous sodium hydroxide solution (pH ˜12), dried and concentrated under reduced pressure. The residue was purified by chromatography (methanol/dichloromethane) to give a gum which was dissolved in dichloromethane and methanol, treated with hydrogen chloride (in ether, 2M) then concentrated under reduced pressure to give the title compound as its hydrochloride salt-beige solid (0.22 mmol, 83 mg, 22% yield). M+H 341.1.

Provenance & Evidence