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

HRID 2288736
Notes
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Reaction equation

HRID 2288736 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[N:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)=[N:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:30]2[CH2:29][CH2:28][N:27]([C:25]([CH:22]3[CH2:23][CH2:24][N:19]([C:16]4[CH:17]=[CH:18][N:13]=[CH:14][N:15]=4)[CH2:20][CH2:21]3)=[O:26])[CH2:32][CH2:31]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 186979701-[1-(4-Pyrimidinyl)-4-piperidylcarbonyl]piperazine

Product 1

HCID 186980611-(4-Cyanobenzenesulphonyl)-4-[1-(4-pyrimidinyl)piperidin-4-ylcarbonyl]piperazineYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

Procedure

A solution of 4 -cyanobenzenesulphonyl chloride (363 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-cyanobenzenesulphonyl)-4-[1-(4-pyrimidinyl)piperidin-4-ylcarbonyl]piperazine (280 mg), mp 180-181° 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-99c2bb54f29b4455b3a2cca07624d5a8
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