Benzoyl chloride → N-(2-phenylpropyl)benzamide

HRID 1910340Notes

Reaction equation

HRID 1910340 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:4].C(N(CC)CC)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[C:5]1([CH:3]([CH3:4])[CH2:2][NH:1][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 113982-Phenylpropylamine

Product 1

HCID 4058764N-(2-phenylpropyl)benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1-amino-2-phenylpropane (25.0 g, 0.185 mol) and triethylamine (18.2 g, 0.185 mol) in 150 mL of chloroform was added dropwise, a solution of benzoyl chloride (26.0 g, 0.185 mol) in 150 mL of chloroform under nitrogen. After completion of the addition, the reaction mixture was heated at reflux for 1 hour. The solution was then washed with water and the organic layer dried over magnesium sulfate. Removal of the solvent yielded 42.0 g (95%) of N-(2-phenylpropyl)benzamide as a white powder.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 1 hour
  4. washThe solution was then washed with water
  5. dry with materialthe organic layer dried over magnesium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-f28b2925d9724ac5aca770d1b8cd6aaa
Source dataset
uspto-grants-2013_12
Patent number
US08603645B2

Reaction notes

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