Water → N-(4-((4-(4,6-dimethylpyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide

HRID 1282158Notes

Reaction equation

HRID 1282158 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:10][CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:20]1[N:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:27][C:22]1[CH:23]=[C:24]([CH3:26])[N:25]=[C:20]([N:4]2[CH2:5][CH2:6][N:1]([CH2:7][C:8]3[CH:9]=[CH:10][C:11]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=3)[CH2:2][CH2:3]2)[N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 205502-Chloro-4,6-dimethylpyrimidineHCID 18423078N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide

Product 1

HCID 18423020N-(4-((4-(4,6-dimethylpyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamideYield 45.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide (1.7 g) obtained in Example 88(2), 2-chloro-4,6-dimethylpyrimidine (1.0 g) and potassium carbonate (3.0 g) in acetonitrile (50 ml) was refluxed under heating for 7 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a yellow oil. The obtained yellow oil was purified by silica gel column chromatography (developing solvent; chloroform:methanol=20:1) and crystallized from diisopropyl ether and recrystallized from ethyl acetate-hexane to give the title compound (1.1 g) as white crystals.

Workup

  1. temperatureunder heating for 7 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give a yellow oil
  7. customThe obtained yellow oil was purified by silica gel column chromatography (developing solvent; chloroform:methanol=20:1)
  8. customcrystallized from diisopropyl ether
  9. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-914aaea20cc54cd7aa8f8af056776dad
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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