Water → N-(4-((4-(2-chloropyrimidin-4-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide

HRID 1282165Notes

Reaction equation

HRID 1282165 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:19][C:20]1[N:25]=[C:24]([Cl:26])[CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Cl:19][C:20]1[N:25]=[C:24]([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)[CH:23]=[CH:22][N:21]=1.[Cl:26][C:24]1[CH:23]=[CH:22][N:21]=[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:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 18423078N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide

Product 2

HCID 18423011N-(4-((4-(2-chloropyrimidin-4-yl)piperazin-1-yl)methyl)phenylmethyl)acetamideHCID 18423034N-(4-((4-(4-chloropyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of N-(4-((piperazin-1-yl)methyl)-phenylmethyl)acetamide (1.0 g) obtained in Example 78(2) and 2,4-dichloropyrimidine (0.60 g) in acetonitrile (20 ml) was added potassium carbonate (0.84 9) and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water (200 ml) and extracted with ethyl acetate (100 ml). The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:methanol=20:1-10:1) to give N-(4-((4-(2-chloropyrimidin-4-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide (0.61 g) as white crystals and N-(4-((4-(4-chloropyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide (10 mg) as white crystals. N-(4-((4-(2-chloropyrimidin-4-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide.

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:methanol=20:1-10:1)

Sources & evidence

ORD record
ord-06afe959a92a453d9908e8fca2d01b57
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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