Dimethylformamide → Oxalic acid--1-[4-(benzenesulfonyl)-4-phenylbutyl]-4-phenylpiperazine (1/1)

HRID 1112409Notes

Reaction equation

HRID 1112409 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[C:21]1([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:33](=[O:36])([O-:35])[O-].[Na+].[Na+].CN(C)[CH:41]=[O:42]>O>[C:41]([OH:42])(=[O:7])[C:33]([OH:35])=[O:36].[C:15]1([CH:5]([S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:4][CH2:3][CH2:2][N:30]2[CH2:31][CH2:32][N:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:28][CH2:29]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 70961-PhenylpiperazineHCID 10340Sodium CarbonateHCID 22763811[1-(Benzenesulfonyl)-4-chlorobutyl]benzene

Product 1

HCID 22763783Oxalic acid--1-[4-(benzenesulfonyl)-4-phenylbutyl]-4-phenylpiperazine (1/1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.16 g of 1-chloro-4-phenyl-4-phenylsulfonylbutane, 4.25 g of 1-phenylpiperazine, 3.5 of sodium carbonate and 80 ml of dimethylformamide was refluxed with stirring for 23 hours. After cooling, water was added to the reaction mixture. The resulting mixture was extracted with chloroform, and the extract was washed with a 10% aqueous hydrochloric acid solution and with an aqueous potassium carbonate solution. To the organic layer was added 1.8 g of oxalic acid. The resulting oxalate was purified with 60% ethanol to give 6 g of 1-(4-phenyl-4-phenylsulfonylbutyl)-4-phenylpiperazine oxalate as white crystals, melting at 179°-181° C with decomposition.

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. extractionThe resulting mixture was extracted with chloroform
  4. washthe extract was washed with a 10% aqueous hydrochloric acid solution and with an aqueous potassium carbonate solution
  5. additionTo the organic layer was added 1.8 g of oxalic acid
  6. customThe resulting oxalate was purified with 60% ethanol

Sources & evidence

ORD record
ord-048b3a994b2644e5ac44c1e92840d2a3
Source dataset
uspto-grants-1978_10
Patent number
US04122178

Reaction notes

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