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

HRID 2251268Notes

Reaction equation

HRID 2251268 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-5b926c5d98dc4d8082ab72d854a5ee5b
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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