Benzylamine → 3-[4-(benzylaminomethyl)phenyl]-N-(4'-chlorobiphenyl-4-yl)propionamide

HRID 735188Notes

Reaction equation

HRID 735188 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.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:27]([NH:34][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)=[O:26])=[CH:19][CH:20]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 68815887N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)propionamide

Product 1

HCID 578458603-[4-(benzylaminomethyl)phenyl]-N-(4'-chlorobiphenyl-4-yl)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, 16 mg (0.15 mmol) of benzylamine, 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. The residue is purified by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia (30:1:0.1)). Yield: 23 mg (40% of theory); melting point: 176° C.; C29H27ClN2O (M=454.99); calc.: molecular ion peak (M+H)+: 455/57 (Cl); found: molecular ion peak (M+H)+: 455/57 (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
  6. customThe residue is purified by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia (30:1:0.1))

Sources & evidence

ORD record
ord-cc5ed602019d49d2a8b30f365ead51bd
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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