Potassium Carbonate → HCID 67128486, compound

HRID 2382256Notes

Reaction equation

HRID 2382256 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-d6fec22c418747cca0c2643f682d8a2c
Source dataset
uspto-grants-2012_09
Patent number
US08258316B2

Reaction notes

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