Ammonia → 4-(4-Chlorophenyl)butanamide

HRID 1021392Notes

Reaction equation

HRID 1021392 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1.O.O[N:16]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N.CO>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH2:16])=[O:13])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 887MethanolHCID 2597404-(4-Chlorophenyl)butyric acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 110743574-(4-Chlorophenyl)butanamideYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(4-chlorophenyl)butanoic acid (3.97 g, 20.0 mmol) and 1-hydroxybenzotriazole hydrate (3.37 g, 22.0 mmol) in N,N-dimethylformamide (40 mL) at ambient temperature was added solid 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.21 g, 22 mmol). The resulting mixture was stirred at ambient temperature for 25 minutes, and a solution of ammonia in methanol (7M, 14.3 mL, 100 mmol) was added. After stirring at ambient temperature for a further 15 minutes, the reaction mixture was diluted with water (400 mL) and extracted with chloroform (100 mL) The organic layer was dried over sodium sulfate and concentrated. The residual oil was triturated with hexane to afford a solid, which was collected by filtration, washed with hexane, and dried under vacuum to afford 4-(4-chlorophenyl)butanamide as an off-white powder (2.40 g, 61% yield).

Workup

  1. stirringAfter stirring at ambient temperature for a further 15 minutes
  2. extractionextracted with chloroform (100 mL) The organic layer
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residual oil was triturated with hexane
  6. customto afford a solid, which
  7. filtrationwas collected by filtration
  8. washwashed with hexane
  9. customdried under vacuum

Sources & evidence

ORD record
ord-866077082ec54d058c110ce3fd5dd035
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

Loading…