Benzylamine → n-Benzyl-4-hydroxy-4-phenylbutanamide

HRID 429174Notes

Reaction equation

HRID 429174 reaction equation
[C:1]1([CH:7]2[O:12][C:10](=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1C=CC=CC=1>[CH2:13]([NH:20][C:10](=[O:11])[CH2:9][CH2:8][CH:7]([OH:12])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7504Benzylamine2×HCID 13884gamma-Phenyl-gamma-butyrolactone

Product 1

HCID 288829n-Benzyl-4-hydroxy-4-phenylbutanamideYield 72%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of γ-phenyl-γ-butyrolactone (5.17 g, 31.8 mmol) and benzylamine (3.48 ml, 31.8 mmol) in 200 ml of benzene was refluxed under a nitrogen atmosphere for 20 hours. An additional 1.75 ml (16.0 mmol) of benzylamine was added and the solution refluxed for 24 hours. When the reaction was partitioned with 1 N HCl a white solid precipitated. The solid was collected by filtration and dried to give N-benzyl-4-hydroxy-4-phenyl-butyramide (6.12 g, 72%) as a white solid, mp 92-94° C.

Workup

  1. temperaturethe solution refluxed for 24 hours
  2. customWhen the reaction was partitioned with 1 N HCl a white solid
  3. customprecipitated
  4. filtrationThe solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-1091e9f0e3354d51a6144f6cff0fec18
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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