Ethyl Acetate → Rac-3-methyl-4-(4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1820813Notes

Reaction equation

HRID 1820813 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH:21]([CH3:25])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)[CH:21]([CH3:25])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylate

Product 1

HCID 59793643Rac-3-methyl-4-(4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl esterYield 30.1%

Reagents, catalysts & solvents 2

HCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To 1-bromo-4-trifluoromethyl-benzene (1 g), rac-3-Methyl-piperazine-1-carboxylic acid tert-butyl ester (1 g), in toluene (10 mL) was added sodium tert-butylate (0.6 g), 2-(dicyclohexylphosphino)biphenyl (31 mg), and tris(dibenzylideneacetone)Pd—CHCl3 (23 mg). The reaction mixture was then stirred at 80° C. overnight. Ethyl acetate was then added to the reaction mixture. Solids were filtered off. The filtrate was then concentrated in vacuo, and the residue was purified by column chromatography to yield 0.46 g of the title compound. MS (m/e): 345.2 (M+H+, 100%)

Workup

  1. filtrationSolids were filtered off
  2. concentrationThe filtrate was then concentrated in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f3d0a4bbb12544dda376218bd9838a17
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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