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Triethylamine → 1-(4-Cyanobenzoyl)-4-[1-(4-pyrimidinyl)piperidin-4-ylcarbonyl] piperazine

HRID 2288744
Notes
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Reaction equation

HRID 2288744 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[N:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[O:25])[CH2:20][CH2:19]2)=[N:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:29]2[CH2:28][CH2:27][N:26]([C:24]([CH:21]3[CH2:22][CH2:23][N:18]([C:15]4[CH:16]=[CH:17][N:12]=[CH:13][N:14]=4)[CH2:19][CH2:20]3)=[O:25])[CH2:31][CH2:30]2)=[O:8])=[CH:5][CH:4]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 186979701-[1-(4-Pyrimidinyl)-4-piperidylcarbonyl]piperazine

Product 1

HCID 186980561-(4-Cyanobenzoyl)-4-[1-(4-pyrimidinyl)piperidin-4-ylcarbonyl] piperazineYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent
2×

Procedure

A solution of 4-cyanobenzoyl chloride (298 mg) in methylene chloride (10 ml) was added to a stirred mixture of 1-[1(4-pyrimidinyl) piperidin-4-ylcarbonyl]piperazine (412.5 mg) and triethylamine (0.28 ml) in methylene chloride (15 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. The mixture was partitioned between methylene chloride and water. The organic phase was washed with water, dried (Na2SO4) and evaporated. The residue was purified by column chromatography using 0.5% methanol in methylene chloride. Recrystallisation from ethyl acetate/hexane gave, as a solid 1-(4-cyanobenzoyl)-4-[1-(4-pyrimidinyl)piperidin-4-ylcarbonyl] piperazine (280 mg): mpt 192-193° C.;

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. washThe organic phase was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. customRecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-038e4a9a567d41dabd787e6020cf9e75
Source dataset
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06090813

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes