Réaction #1170

Équation de réaction

ammonia

Cyclopentylacetic acid

thionyl chloride

DMF

→

cyclopentylacetamide

Rendement 52.0%

Solvants

Dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGthe mixture stirred for 0.5 h
3. 3
   ExtractionThe solution was extracted with CH2Cl2 (3×)
4. 4
   Lavagethe combined extracts washed with 1N HCl
5. 5
   Séchagedried over MgSO4
6. 6
   Concentrationconcentrated

Mode opératoire

Cyclopentylacetic acid (5.2 g, 41 mmol) and thionyl chloride (10 mL) were combined then DMF (0.2 mL) was added and the solution was stirred 1.5 h at R.T. Dichloromethane (10 mL) was added and the solution cooled in an ice bath whereupon 25% aqueous ammonia (30 mL) was added and the mixture stirred for 0.5 h. The solution was extracted with CH2Cl2 (3×) and the combined extracts washed with 1N HCl, dried over MgSO4, and concentrated to give cyclopentylacetamide (2.699 g, 52%). [1H]-NMR(CDCl3) consistent with structure.

Source