Sulfuric Acid → 1-(4-Methoxyphenyl)-2-methylpiperazine

HRID 648494Notes

Reaction equation

HRID 648494 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:16][CH:15]2[CH3:30])=[CH:10][CH:9]=1.[OH-].[Na+]>O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH3:30])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 3727602HCID 3727602, compound

Product 1

HCID 27237771-(4-Methoxyphenyl)-2-methylpiperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 11.9 parts of water was added dropwise 11.5 parts of sulfuric acid with stirring and while cooling. Then there was added portionwise 4.6 parts of dl-1-(4-methoxyphenyl)-2-methyl-4-(4-methylphenylsulfonyl)piperazine and after addition was complete, the whole was stirred and refluxed for 20 hours. After cooling the reaction mixture was poured onto crushed ice. The whole was alkalized with sodium hydroxide solution 15N and extracted three times with 4-methyl-2-pentanone. The combined extracts were dried over potassium carbonate and evaporated. The oily residue was distilled in vacuo, yielding 1.7 parts of oily 1-(4-methoxyphenyl)-2-methylpiperazine; bp. 144°-147° C. at 0.3 mm pressure; nD20 =1.5633; d2020 =1.0782 (76).

Workup

  1. temperaturewhile cooling
  2. additionafter addition
  3. stirringthe whole was stirred
  4. temperaturerefluxed for 20 hours
  5. temperatureAfter cooling the reaction mixture
  6. additionwas poured
  7. customonto crushed ice
  8. extractionextracted three times with 4-methyl-2-pentanone
  9. dry with materialThe combined extracts were dried over potassium carbonate
  10. customevaporated
  11. distillationThe oily residue was distilled in vacuo

Sources & evidence

ORD record
ord-ee5da002dbff41919ff8879b242d8853
Source dataset
uspto-grants-1988_04
Patent number
US04735942

Reaction notes

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