N,N-dimethyl-4-(2-fluoro-5-bromobenzyloxy)butylamine → N-methyl-4-[2-fluoro-5-bromobenzyloxy]butylamine

In a 10 ml flask, under a nitrogen atmosphere, N,N-dimethyl-4-[2-fluoro-5-bromobenzyloxy]butylamine (215 mg, 0.707 mmol) was dissolved in dichloroethane (2.0 ml). To this solution ACE•Cl (0.305 ml, 2.83 mmol) was added and the resulting mixture was heated to reflux. The reaction mixture was refluxed for four hours. The prgress of the reaciton was monitored by thin layer chromatography. The mixture was refluxed for an additional 16 hours. The solvents were removed in vacuo and the residue was taken up in methanol. The methanol solution was refluxed for 1.5 hours and the solvents were removed by evaporation. The residue was partitioned between 1 M potassium carbonate and methylene chloride. The aqueous fraction was back extracted with methylene chloride. The organic fractions were combined and dried over sodium sulfate. The solvents were removed in vacuo. The title intermediate was further purified by liquid chromatography.

1. temperaturethe resulting mixture was heated to reflux
2. temperatureThe reaction mixture was refluxed for four hours
3. temperatureThe mixture was refluxed for an additional 16 hours
4. customThe solvents were removed in vacuo
5. temperatureThe methanol solution was refluxed for 1.5 hours
6. customthe solvents were removed by evaporation
7. customThe residue 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 liquid chromatography

ORD record

ord-503bd173f3014c0f95d2b27d3ffb106a

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1