Toluene → N-(2,6-Diisopropylphenyl)-2-[2-(4-phenylpiperazinyl)ethylsulfonyl]acetamide

HRID 36765Notes

Reaction equation

HRID 36765 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:22])[CH2:15][S:16]([CH2:19][CH2:20]Cl)(=[O:18])=[O:17])([CH3:3])[CH3:2].[C:23]1([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:22])[CH2:15][S:16]([CH2:19][CH2:20][N:32]1[CH2:33][CH2:34][N:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:30][CH2:31]1)(=[O:18])=[O:17])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 70961-PhenylpiperazineHCID 19937765N-(2,6-diisopropylphenyl)-2(2-chloroethylsulfonyl)acetamide

Product 1

HCID 19937768N-(2,6-Diisopropylphenyl)-2-[2-(4-phenylpiperazinyl)ethylsulfonyl]acetamideYield 70.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.46 g of N-(2,6-diisopropylphenyl)-2(2-chloroethylsulfonyl)acetamide synthesized in (1) above, 1.62 g of N-phenylpiperazine, and 50 ml of toluene was heated under reflux for 4 hours. To the reaction mixture was added 100 ml of ethyl acetate, and the mixture was washed successively with a sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography using a mixture of ethyl acetate and hexane at a ratio varying from 1:1 to 1:0 as a developing solvent. The solvent was evaporated, and the residue was dissolved in ethyl acetate and crystallized from a 4N hydrochloric acid solution in ethyl acetate to obtain 3.33 g of the title compound as white powder (m.p.=197.0°-200.0° C.).

Workup

  1. temperatureunder reflux for 4 hours
  2. washthe mixture was washed successively with a sodium hydrogencarbonate aqueous solution
  3. dry with materiala saturated sodium chloride aqueous solution, and dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additiona mixture of ethyl acetate and hexane at a ratio
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. customcrystallized from a 4N hydrochloric acid solution in ethyl acetate

Sources & evidence

ORD record
ord-2c01800daad5483f8931d0b7feb74107
Source dataset
uspto-grants-1995_05
Patent number
US05416212

Reaction notes

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