1-[2-Nitro-4-(trifluoromethyl)phenyl]piperazine → N-(6-chloro-2-phenylpyrimidin-4-yl)-2-piperidin-1-ylacetamide

HRID 1783330Notes

Reaction equation

HRID 1783330 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([Cl:12])[N:9]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:7]=1)=[O:4].FC(F)(F)C1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31]NCC2)=C([N+]([O-])=O)C=1>C(#N)C>[Cl:12][C:10]1[N:9]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:27]2[CH2:24][CH2:25][CH2:26][CH2:31][CH2:32]2)[CH:11]=1

Participants

4

Reactant 2

HCID 27714071-[2-Nitro-4-(trifluoromethyl)phenyl]piperazineHCID 223791512-bromo-N-(6-chloro-2-phenylpyrimidin-4-yl)acetamide

Product 1

HCID 22353518N-(6-chloro-2-phenylpyrimidin-4-yl)-2-piperidin-1-ylacetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-N-(6-chloro-2-phenylpyrimidin-4-yl)acetamide (100 mg) was dissolved in acetonitrile (5 ml) and (4-trifluromethyl-2-nitrophenyl)piperazine (253 mg) added. The solution was stirred overnight at room temperature. After this time the solvent was removed in vacuo. Purification by flash chromatography on silica gel eluting with a mixture of dichloromethane and methanol (98:2, then 93:7 v/v) afforded the title compound. m/z (ES+) 521 (MH)+

Workup

  1. customAfter this time the solvent was removed in vacuo
  2. customPurification by flash chromatography on silica gel eluting
  3. additionwith a mixture of dichloromethane and methanol (98:2

Sources & evidence

ORD record
ord-5c6c184e1d684d56a0e5c98b1dbafb7f
Source dataset
uspto-grants-2009_03
Patent number
US07501407B2

Reaction notes

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