Potassium Carbonate → HCID 67128486, compound

HRID 1971771Notes

Reaction equation

HRID 1971771 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].Br[C:24]([CH3:36])([CH3:35])[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>CC#N.CCOC(C)=O>[CH3:35][C:24]([N:12]1[CH2:11][CH2:10][N:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][N:7]=2)[CH2:14][CH2:13]1)([CH3:36])[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6676181-(5-Trifluoromethyl-pyridin-2-yl)-piperazineHCID 12558195HCID 12558195, compound

Product 1

HCID 67128486HCID 67128486, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[5-(trifluoromethyl)pyrid-2-yl]piperazine (554 mgs, 2.4 mmol) in CH3CN (5 mL) and K2CO3 (1.1 g, 8.0 mmol) was added benzyl 2-bromo-2-methylpropanoate (512 mgs, 2.0 mmol). The reaction mixture was heated to 80° C. After 14 hours, the reaction mixture was cooled to room temperature, diluted with EtOAc, stirred and filtered. The filtrate was then concentrated and purified by flash chromatography on silica gel with elution using 3% MeOH/CH2Cl2 to give Benzyl 2-methyl-2-(4-(5-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propanoate.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was then concentrated
  4. custompurified by flash chromatography on silica gel with elution

Sources & evidence

ORD record
ord-ab70751a2dd4441587c27f786ed2da7f
Source dataset
uspto-grants-2013_04
Patent number
US08431610B2

Reaction notes

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