Potassium Sodium Tartrate → N-(2-Chloro-3-trifluoromethylbenzyl)-2-(2-chlorophenyl)propylamine

HRID 902724Notes

Reaction equation

HRID 902724 reaction equation
[Cl:1][C:2]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][C:6](=O)[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])[CH3:8].[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.CCCCCC.CCOCC>[Cl:1][C:2]1[C:20]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])[CH3:8]

Participants

7

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 69254638N-(2-Chloro-3-trifluoromethylbenzyl)-2-(2-chlorophenyl)propionamide

Product 1

HCID 69252183N-(2-Chloro-3-trifluoromethylbenzyl)-2-(2-chlorophenyl)propylamine

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A solution of N-(2-chloro-3-trifluoromethylbenzyl)-2-(2-chlorophenyl)propionamide (265 mg, 0.7 mmole) in 40 mL of toluene was treated with diisobutyl aluminum hydride (5 mL of a 1N solution in hexane), and the reaction was stirred for 90 minutes. The reaction was diluted with 20 mL of Et2O, a concentrated aqueous solution of Rochelle salt was added, and the mixture stirred for 60 minutes, at which time the emulsion had broken apart. The organic layer was separated, washed with H2O, aqueous Rochelle salt, dried and the solvent removed, and gave the titled compound, 221 mg (87%). MS (ESI) 362 (MH+).

Workup

  1. stirringthe mixture stirred for 60 minutes, at which time the emulsion
  2. customThe organic layer was separated
  3. washwashed with H2O, aqueous Rochelle salt
  4. customdried
  5. customthe solvent removed

Sources & evidence

ORD record
ord-c08b500b8b534aef85b5c6e605de45b8
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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