Sulfuric Acid → 1-(2,4,6-Trimethylphenyl)piperazine

HRID 486434

Reaction equation

HRID 486434 reaction equation
CC1C=CC(S([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])[CH2:13][CH2:12]2)(=O)=O)=CC=1.S(=O)(=O)(O)O.[OH-].[NH4+]>O>[CH3:23][C:22]1[CH:21]=[C:20]([CH3:24])[CH:19]=[C:18]([CH3:25])[C:17]=1[N:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 166456031-Mesityl-4-[(4-methylphenyl)sulfonyl]piperazine

Product 1

HCID 27608221-(2,4,6-Trimethylphenyl)piperazineYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 180 parts of 1-[(4-methylphenyl)sulfonyl]-4-(2,4,6-trimethylphenyl)piperazine and 450 parts of water were added dropwise 675 parts of sulfuric acid. The whole was stirred and refluxed for 4 hours. After cooling, the whole was treated with an ammonium hydroxide solution. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 70 parts (69%) of 1-(2,4,6-trimethylphenyl)piperazine as a residue (intermediate 14).

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureAfter cooling
  3. extractionThe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9c3e9e9c6f994e3997e6d57254668174
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Linked notes

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