Benzoyl chloride → N-[2-(3,4-dimethoxyphenyl)-1-(3-pyridyl)ethyl]benzamide

HRID 464318Notes

Reaction equation

HRID 464318 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH2:20][CH:21]([NH2:28])[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH3:19].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH2:20][CH:21]([NH:28][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 133198932-(3,4-Dimethoxyphenyl)-1-(3-pyridyl)ethylamine

Product 1

HCID 13319894N-[2-(3,4-dimethoxyphenyl)-1-(3-pyridyl)ethyl]benzamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

9.75 g of benzoyl chloride in 10 ml of chloroform are added, cooling in ice, to 14.9 g of 2-(3,4-dimethoxyphenyl)-1-(3-pyridyl)ethylamine and 12.1 g of triethylamine in 200 ml of chloroform. The mixture is stirred at room temperature for 4 hours, the chloroform is distilled out in vacuo and the residue is washed with toluene and water. 18.5 g of the amide of melting point 156°-158° C. are obtained.

Workup

  1. distillationthe chloroform is distilled out in vacuo
  2. washthe residue is washed with toluene and water

Sources & evidence

ORD record
ord-55fdd6bbe0aa49aa8485e66ac7ef46b9
Source dataset
uspto-grants-1985_10
Patent number
US04547508

Reaction notes

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