Water → HCID 17796369, compound

HRID 1282156Notes

Reaction equation

HRID 1282156 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]1[N:21]=[C:20]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:19]=[C:18]([O:28][CH3:29])[N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:14][O:15][C:16]1[N:21]=[C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=3)[CH2:24][CH2:23]2)[CH:19]=[C:18]([O:28][CH3:29])[N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15550682N-((4-(chloromethyl)phenyl)methyl)acetamideHCID 18423149HCID 18423149, compound

Product 1

HCID 17796369HCID 17796369, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chloromethylphenylmethyl)acetamide (1.0 g), 1-(2,6-dimethoxypyrimidin-4-yl)piperazine (1.1 g) and potassium carbonate (1.0 g) in dimethylformamide (10 ml) was stirred at 80° C. for 2 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a brown oil (2.1 g). The obtained brown oil was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1) and crystallized from ethyl acetate:diisopropyl ether (1:2, 30 ml) to give the title compound (1.0 g) as white crystals, m.p.=89-90° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8c881983babc4e65be57292fd5c1ce51
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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