Dimethylamine, hydrochloride → 5-(dimethylamino)pentan-2-one

A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation.

1. temperatureat reflux for 2 hours
2. temperatureThe reaction mixture was then cooled to room temperature
3. custompartitioned between water and dichloromethane
4. customThe phases were separated
5. extractionthe aqueous phase again extracted with dichloromethane
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. washeluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide
9. concentrationconcentrated under reduced pressure

ORD record

ord-e56e5855151d4236a3a9f5392449b3f9

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05962473