Dimethylamine → HCID 21196108, compound

Temperature

-78 °C

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.

1. customthe tube was sealed
2. temperatureThe mixture was warmed to 85° C.
3. temperatureThe mixture was cooled to ambient temperature
4. stirringstirred for another twelve hours
5. customThe mixture was bubbled with nitrogen gas for fifteen minutes
6. customto remove excess dimethylamine
7. customThe reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride
8. extractionThe aqueous fraction was back-extracted with methylene chloride
9. dry with materialdried over sodium sulfate
10. customthe solvents were removed in vacuo
11. customThe title intermediate was further purified by silica gel

ORD record

ord-d1e7894136c74d0488f3a0fd2d8b4a8d

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1