Potassium Carbonate → N-(4'-chlorobiphenyl-4-yl)-3-{4-[(methylpyridin-4-ylmethylamino)methyl]phenyl}propionamide

HRID 735187Notes

Reaction equation

HRID 735187 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:27][NH:28][CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])[CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:24][N:28]([CH3:27])[CH2:29][C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)=[CH:22][CH:23]=3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81436N-Methylpyridine-4-methylamineHCID 68815887N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)propionamide

Product 1

HCID 57845791N-(4'-chlorobiphenyl-4-yl)-3-{4-[(methylpyridin-4-ylmethylamino)methyl]phenyl}propionamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A reaction mixture of 70 mg (0.18 mmol) of N-(4′-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)propionamide, 18 mg (0.15 mmol) of methylpyridin-4-ylmethylamine, and 41 mg (0.3 mmol) of potassium carbonate in 5 mL of acetone is agitated for 24 hours at reflux temperature. The reaction mixture is evaporated down. The residue is triturated with water and diisopropyl ether, suction filtered and dried in the air. Yield: 52 mg (87% of theory); melting point: 102° C.; C29H28ClN3O (M=470.01); calc.: molecular ion peak (M+H)+: 470/72 (Cl); found: molecular ion peak (M+H)+: 470/72 (Cl).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated down
  3. customThe residue is triturated with water and diisopropyl ether, suction
  4. filtrationfiltered
  5. customdried in the air

Sources & evidence

ORD record
ord-1f870b5bafd5475bb4627194e1109b1c
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…