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

HRID 1282139Notes

Reaction equation

HRID 1282139 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:16]1([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])=[CH:25][CH:24]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O>C(#N)C>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([N:19]2[CH2:18][CH2:17][N:16]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])=[CH:27][CH:28]=3)[CH2:21][CH2:20]2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 773782,4,6-TrichloropyrimidineHCID 18423078N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide

Product 1

HCID 18423092n-(4-((4-(4,6-Dichloropyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamideYield 100.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2,4,6-trichloropyrimidine (1.0 g) and potassium carbonate (0.84 g) in acetonitrile (20 ml) was added a solution of N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide (1.0 g) obtained in Example 78(2) in acetonitrile (20 ml) under ice-cooling over 5 min. The mixture was stirred at the same temperature for 30 min. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-brown oil (1.6g). The obtained pale-brown oil was purified by silica gel column chromatography (developing solvent; chloroform:methanol=50:1) to give a crude purification product (0.28 g) of N-(4-((4-(4,6-dichloropyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide and a crude purification product (0.9 g) of N-(4-((4-(2,6-dichloropyriinidin-4-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide. The crude purification product of N-(4-((4-(4,6-dichloropyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide was crystallized from ethyl acetate:hexane to give the title compound (0.2 g) as white crystals, m.p.=139-140° C.

Workup

  1. temperaturecooling over 5 min
  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

Sources & evidence

ORD record
ord-02e734a8f6334739ab171b355421ea51
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

Loading…