Sodium hydride → HCID 69609138, compound

Participants

Reaction Steps

To a heterogenous mixture of unwashed 60% NaH dispersed in mineral oil (96.5 mg, 2.41 mmol) in DMF (3 mL) was added 8-[2-[2-(2-thienyl)phenyl]ethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (prepared as in Example 5) (208.8 mg, 0.500 mmol). The mixture was stirred until H2 gas evolution was observed to stop (30 min), then treated with N,N-dimethylaminoethyl chloride hydrochloride (158 mg, 1.10 mmol). The resulting reaction mixture was stirred for an additional 18 h under argon atmosphere. The reaction was quenched with aqueous NH4Cl (50 mL), and the crude product was extracted into CHCl3 (2×40 mL). The organic extracts were washed with H2O (5×50 mL), dried over Na2SO4, filtered and concentrated to a crude oil. The crude oil was washed with hexane (3×50 mL) to remove mineral oil, then purified by Tapered prep TLC (6% MeOH in CHCl3) to yield title compound as a free base. The free base was dissolved in CHCl3 (15 mL) and treated with 1.0 mL of 1N HCl in Et2O. HCL salt was precipitated by addition of Et2O, collected by filtration and dried in the vacuum oven at 60° C. for 18 h to yield the title compound as a white amorphous solid.

Provenance & Evidence