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Water → N-(1-{4-[(3,5-dimethyl-4-pyrimidin-2-ylpiperazin-1-yl)methyl]phenyl}cyclopropyl)acetamide

HRID 76349
Notes
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Reaction equation

HRID 76349 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH:12][C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl.[CH3:17][CH:18]1[CH2:23][NH:22][CH2:21][CH:20]([CH3:24])[N:19]1[C:25]1[N:30]=[CH:29][CH:28]=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:24][CH:20]1[N:19]([C:25]2[N:26]=[CH:27][CH:28]=[CH:29][N:30]=2)[CH:18]([CH3:17])[CH2:23][N:22]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3([NH:12][C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]3)=[CH:5][CH:4]=2)[CH2:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18423039N-(1-(4-chloromethylphenyl)cyclopropyl)acetamideHCID 684321412-(2,6-Dimethylpiperazin-1-yl)pyrimidine hydrochloride

Product 1

HCID 25133308N-(1-{4-[(3,5-dimethyl-4-pyrimidin-2-ylpiperazin-1-yl)methyl]phenyl}cyclopropyl)acetamideYield 647.6%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-[1-(4-Chloromethylphenyl)cyclopropyl]acetamide (22.3 mg) and 2-(2,6-dimethylpiperazin-1-yl)pyrimidine hydrochloride (265 mg) were dissolved in N,N-dimethylformamide (10 mL), potassium carbonate (415 mg) was added and the mixture was stirred at 80° C. for 8 hr. Water (20 mL) was added and the mixture was stirred, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate) to give the title compound (245 mg).

Workup

  1. stirringthe mixture was stirred
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-02fbb717c0d143ec9697583aa9df3cc6
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835631B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes