Phenethylamine → 2-bromo-N-(2-phenylethyl)benzamide

HRID 1162971

Reaction equation

HRID 1162971 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Br:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>ClCCl>[C:1]1([CH2:7][CH2:8][NH:9][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[Br:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 235422-Bromobenzoyl chloride

Product 1

HCID 6738402-bromo-N-(2-phenylethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 62.7 ml (500 mmol) of phenylethylamine, 70.4 ml (506 mmol) of triethylamine and 150 ml of dichloromethane was admixed dropwise at 0° C. with a solution of 109.2 g of 2-bromobenzoyl chloride in 50 ml of dichloromethane with good stirring at such a rate that the temperature did not exceed 30° C. Subsequently, the mixture was stirred at room temperature for a further 1 h. The colorless solid thus obtained was filtered off with suction, washed three times with 200 ml of dichloromethane and dried under reduced pressure. The yield at a purity of approx. 99.0% was 138.2 g (453 mmol), 90.7% of theory.

Workup

  1. customdid not exceed 30° C
  2. stirringSubsequently, the mixture was stirred at room temperature for a further 1 h
  3. customThe colorless solid thus obtained
  4. filtrationwas filtered off with suction
  5. washwashed three times with 200 ml of dichloromethane
  6. customdried under reduced pressure
  7. customThe yield at a purity of approx. 99.0%

Sources & evidence

ORD record
ord-9e9952705e4e41c7bad252afd7a6403e
Source dataset
uspto-grants-2010_10
Patent number
US07820822B2

Linked notes

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