Water → n-(4-((4-(4,6-Diethoxypyrimidin-2-yl)piperazin-1-yl)methyl)-phenylmethyl)acetamide

HRID 1282179Notes

Reaction equation

HRID 1282179 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.[CH2:14]([O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH3:25])[N:20]=[C:19]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[N:18]=1)[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:24]([O:23][C:21]1[CH:22]=[C:17]([O:16][CH2:14][CH3:15])[N:18]=[C:19]([N:26]2[CH2:31][CH2:30][N:29]([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)[CH2:28][CH2:27]2)[N:20]=1)[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15550682N-((4-(chloromethyl)phenyl)methyl)acetamideHCID 184231681-(4,6-Diethoxypyrimidin-2-yl)piperazine

Product 1

HCID 18423001n-(4-((4-(4,6-Diethoxypyrimidin-2-yl)piperazin-1-yl)methyl)-phenylmethyl)acetamideYield 115.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chloromethylphenylmethyl)acetamide (1.2 g), 1-(4,6-diethoxypyrimidin-2-yl)piperazine (1.7 g) and potassium carbonate (1.3 g) in dimethylformamide (20 ml) was stirred at 80° C. for 4.5 hr. The reaction mixture was poured into water(150 ml) 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 (2.9 g). The obtained brown oil was purified by silica gel column chromatography to give a pale-yellow oil (2.4 g). The obtained pale-yellow oil was crystallized from ethyl acetate/hexane (2:1, 30 ml) to give the title compound (1.7 g) as white crystals, m.p.=119-120° 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-fd766baa0f114d35803b8229213d5240
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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