Triethylamine → 4-(4-Fluorophenyl)-1-[2-(1-phenethylcarbonylpiperidin-4-yl)-ethenylsulphonyl]-piperazine

HRID 895379Notes

Reaction equation

HRID 895379 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][N:22]([S:25]([CH:28]=[CH:29][CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)(=[O:27])=[O:26])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:24][CH2:23][N:22]([S:25]([CH:28]=[CH:29][CH:30]3[CH2:35][CH2:34][N:33]([C:9]([CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[O:10])[CH2:32][CH2:31]3)(=[O:26])=[O:27])[CH2:21][CH2:20]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 541755954-(4-Fluorophenyl)-1-[2-(piperidin-4-yl)-ethenylsulphonyl]-piperazine

Product 1

HCID 545434324-(4-Fluorophenyl)-1-[2-(1-phenethylcarbonylpiperidin-4-yl)-ethenylsulphonyl]-piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Phenylpropionyl chloride (0.21 ml) was added dropwise to a solution of 4-(4-fluorophenyl)-1-[2-(piperidin-4-yl)-ethenylsulphonyl]-piperazine (0.5 g) in dichloromethane containing triethylamine (0.2 ml). The mixture was stirred for 3 hours, evaporated to dryness, diluted with water and extracted with ethyl acetate (2×15 ml). The ethyl acetate extracts were combined and washed with aqueous sodium bicarbonate, water and dried. Removal of the solvent gave 4-(4-fluorophenyl)-1-[2-(1-phenethylcarbonylpiperidin-4-yl)-ethenylsulphonyl]-piperazine as a gum, M+H=486 (485).

Workup

  1. customevaporated to dryness
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate (2×15 ml)
  4. washwashed with aqueous sodium bicarbonate, water
  5. customdried
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-ba656dd9d2fe4c959a8f0b19bde755cb
Source dataset
uspto-grants-2005_07
Patent number
US06916817B1

Reaction notes

Loading…