Ethanol → HCID 2399073, compound

HRID 2164254Notes

Reaction equation

HRID 2164254 reaction equation
Br.Br.[N:3]1([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(O)C.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+]>O>[OH:15][C:12]1[CH:11]=[CH:10][C:9]([N:3]2[CH2:4][CH2:5][N:6]([S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=3)(=[O:28])=[O:27])[CH2:7][CH2:8]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2723591p-(1-Piperazinyl)phenol dihydrobromide

Product 1

HCID 2399073HCID 2399073, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 15.5 parts of 4-(1-piperazinyl)phenol dihydrobromide, 40 parts of ethanol and 75 parts of water are added 15.2 parts of 4-methylbenzenesulfonyl chloride and stirring is continued for 30 minutes at room temperature. Then there are added portionwise 12.6 parts of sodium hydrogen carbonate at 0° C. Upon completion, stirring is continued overnight at room temperature. The precipitated product is filtered off and taken up in alkaline water. The mixture is filtered over hyflo and the filtrate is acidified with acetic acid. The precipitated product is filtered off and taken up in water. The free base is liberated in the conventional manner with a sodium hydroxide solution. The whole is filtered over hyflo and the filtrate is acidified with acetic acid. The precipitated product is filtered off and dried, yielding 4.8 parts of 1-(4-hydroxyphenyl)-4-(4-methylphenylsulfonyl)piperazine; mp. 193.1° C.

Workup

  1. stirringUpon completion, stirring
  2. waitis continued overnight at room temperature
  3. filtrationThe precipitated product is filtered off
  4. filtrationThe mixture is filtered over hyflo
  5. filtrationThe precipitated product is filtered off
  6. filtrationThe whole is filtered over hyflo
  7. filtrationThe precipitated product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-897bb2741ecd4fe5975ef176a9d465c6
Source dataset
uspto-grants-1985_03
Patent number
US04503055

Reaction notes

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