Triethylamine → 1-(4-Cyanophenylsulphonyl)-4-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine

HRID 2288732Notes

Reaction equation

HRID 2288732 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28]([C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1)#[N:29]>ClCCl.N1C=CC=CC=1>[C:28]([C:30]1[CH:31]=[CH:32][C:33]([S:36]([N:18]2[CH2:17][CH2:16][N:15]([C:13]([CH:10]3[CH2:11][CH2:12][N:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)[CH2:8][CH2:9]3)=[O:14])[CH2:20][CH2:19]2)(=[O:38])=[O:37])=[CH:34][CH:35]=1)#[N:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 108022941-(4-Pyridylpiperidin-4-ylcarbonyl)piperazine

Product 1

HCID 105510441-(4-Cyanophenylsulphonyl)-4-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(1-(4-pyridyl)piperdin-4-ylcarbonyl)piperazine (0.411 g) was dissolved in dry dichloromethane (20 mL) and stirred under argon at 0° C. To the resulting solution was added triethylamine (0.56 mL) followed by the dropwise addition of a solution of 4-cyanobenzenesulphonyl chloride (0.33 g, 1.6 mmol) in dry pyridine (20 mL). The reaction was then stirred at 0° C. for 10 minutes and then allowed to warm to room temperature and stirred for a further 1 hour. The reaction was quenched by the removal of the dichloromethane and pyridine solvents by evaporation, taken up in water (60 mL) and then extracted with ethyl acetate (3×50 mL). The organic extracts were then washed with water, brine, dried (MgSO4) and evaporated to dryness. The product was then recrystallised to give 1-(4-cyanophenylsulphonyl)-4-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine as a white, hygroscopic solid m.p. 168-169° C.;

Workup

  1. stirringThe reaction was then stirred at 0° C. for 10 minutes
  2. temperatureto warm to room temperature
  3. stirringstirred for a further 1 hour
  4. customThe reaction was quenched by the removal of the dichloromethane and pyridine solvents by evaporation
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. washThe organic extracts were then washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness
  9. customThe product was then recrystallised

Sources & evidence

ORD record
ord-140fb63321384490a94eca5960883e27
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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