Reaction #452422

Reaction equation

5-chloro-2-pentanone

dimethylamine hydrochloride

potassium carbonate

→

desired product

N,N-dimethyl-5-amino-2-pentanone

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureat reflux for 2 hours
2. 2
   TemperatureThe reaction mixture was then cooled to room temperature
3. 3
   Otherpartitioned between water and dichloromethane
4. 4
   OtherThe phases were separated
5. 5
   Extractionthe aqueous phase again extracted with dichloromethane
6. 6
   Dryingdried over sodium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   Washeluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide
9. 9
   Concentrationconcentrated under reduced pressure

Procedure

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.

Source