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

HRID 2289531Notes

Reaction equation

HRID 2289531 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>ClCCl>[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]

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 6344DichloromethaneSolvent2×

Procedure

A solution of 4-cyanobenzoyl chloride (298 mg) in dichloromethane (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 dichloromethane (15 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. The mixture was partitioned between dichloromethane 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 dichloromethane. Recrystallisation from ethyl acetate/hexane gave, as a solid 1-(4-cyanobenzoyl)-4-[l-(4-pyrimidinyl)-4-piperidylcarbonyl]piperazine (280 mg), mp 192-193° C.;

Workup

  1. customThe mixture was partitioned between dichloromethane 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-33b09d64f68e421a92d44eb1a46cb695
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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