Benzoyl chloride → N-Benzoylbenzylamine

HRID 643238Notes

Reaction equation

HRID 643238 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH2:1]([NH:8][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7504BenzylamineHCID 81531Diisopropylethylamine

Product 1

HCID 73878N-Benzoylbenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzylamine (0.125 mmol) in 5 mL of THF is added diisopropylethyl amine (0.15 mmol) and benzoylchloride (0.10 mmol). The reaction mixture is stirred at room temperature for 1 hour or until TLC analysis shows consumption of the benzoyl chloride. To this mixture is added perfluorsulfonic acid resin prepared in example 8 (3 g, 0.3 mmol/g loading) and the slurry is gently agitated for 1 hour. The slurry is filtered and the resin washed with dichloromethane. The combined filtrates are combined and the solvent removed under reduced pressure to afford N-benzylbenzamide as a solid.

Workup

  1. customconsumption of the benzoyl chloride
  2. additionTo this mixture is added perfluorsulfonic acid resin prepared in example 8 (3 g, 0.3 mmol/g loading)
  3. stirringthe slurry is gently agitated for 1 hour
  4. filtrationThe slurry is filtered
  5. washthe resin washed with dichloromethane
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-cf2ed6fa324145fc8694095a2c7c4aca
Source dataset
uspto-grants-2010_04
Patent number
US07700524B2

Reaction notes

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