HCID 21196091, compound → 3-[(5-Bromo-2-fluorophenyl)methoxy]-N-methyl-1-propanamine

In a 15 m flask, under a nitrogen atmosphere, N,N-dimethyl-3-[2-fluoro-5-bromobenzyloxy]propylamine (351 mg, 1.21 mmol) was dissolved in dichloroethane (3.5 ml). To this solution ACE•Cl (0.78 ml, 7.26 mmol) was added and the resulting mixture was heated to reflux and maintained at this temperature for 18 hours. The reaction mixture was cooled to ambient temperature, and the solvents were removed in vacuo. The residue was taken up in methanol and refluxed for 1.5 hours. The methanol solution was then 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
2. temperatureto reflux
3. temperaturemaintained at this temperature for 18 hours
4. customthe solvents were removed in vacuo
5. temperaturerefluxed for 1.5 hours
6. customThe methanol solution was then partitioned between 1 M potassium carbonate and methylene chloride
7. extractionThe aqueous fraction was back extracted with methylene chloride
8. dry with materialdried over sodium sulfate
9. customThe solvents were removed in vacuo
10. customThe title intermediate was further purified by liquid chromatography

ORD record

ord-cd9170fd940049fd894b1d51c9c5a63a

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1