Dimethylamine → HCID 21196108, compound

Participants

Reaction Conditions

Reaction Steps

In a sealable tube, under a nitrogen atmosphere, 5-[2-fluoro-5-bromobenzyloxy]pentyl chloride (0.380 g, 1.23 mmol) was dissolved in N,N-dimethylformamide (5 ml). To this solution sodium iodide (55 mg, 0.368 mmol) was added and the resulting mixture was cooled to −78° C. To the reaction mixture dimethylamine (precondensed in anhydrous conditions) was added and the tube was sealed. The mixture was warmed to 85° C. and stirred for eight hours. The mixture was cooled to ambient temperature and stirred for another twelve hours. The mixture was bubbled with nitrogen gas for fifteen minutes to remove excess dimethylamine. The reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride. The aqueous fraction was back-extracted with methylene chloride. The organic fractions were combined, dried over sodium sulfate, and the solvents were removed in vacuo. The title intermediate was further purified by silica gel.

Provenance & Evidence