Ammonia → 2-Cyclopentylacetamide

HRID 1074

Reaction equation

HRID 1074 reaction equation
[CH:1]1([CH2:6][C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.C[N:15](C=O)C.N>ClCCl>[CH:1]1([CH2:6][C:7]([NH2:15])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 71606Cyclopentylacetic acid

Product 1

HCID 184256332-CyclopentylacetamideYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. additionwas added
  2. stirringthe mixture stirred for 0.5 h
  3. extractionThe solution was extracted with CH2Cl2 (3×)
  4. washthe combined extracts washed with 1N HCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f02b90c8e56b477c889ab251909baee4
Source dataset
uspto-grants-1998_03
Patent number
US05723490

Linked notes

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