Ethanol → 4-(4-(Methylsulfonyl)piperazin-1-yl)phenol

HRID 614434

Reaction equation

HRID 614434 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.C(=O)([O-])O.[Na+].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>O>[OH:15][C:12]1[CH:11]=[CH:10][C:9]([N:3]2[CH2:4][CH2:5][N:6]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:7][CH2:8]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2723591p-(1-Piperazinyl)phenol dihydrobromide

Product 1

HCID 6400494-(4-(Methylsulfonyl)piperazin-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 12.9 parts of 4-(1-piperazinyl)phenol dihydrobromide, 40 parts of ethanol and 50 parts of water are added 12.6 parts of sodium hydrogen carbonate. Then there are added dropwise 6.4 parts of methanesulfonyl chloride at 0° C. Upon completion, stirring is continued overnight. The precipitated product is filtered off and taken up in water. The whole is alkalized with a sodium hydroxide solution and stirred for 30 minutes at room temperature. The mixture is filtered over hyflo and the filtrate is acidified with acetic acid. The precipitated product is filtered off and dried, yielding 2.8 parts of 1-(4-hydroxyphenyl)-4-(methylsulfonyl)piperazine; mp. 204.9° C.

Workup

  1. filtrationThe precipitated product is filtered off
  2. stirringstirred for 30 minutes at room temperature
  3. filtrationThe mixture is filtered over hyflo
  4. filtrationThe precipitated product is filtered off
  5. customdried

Sources & evidence

ORD record
ord-32f77790464d442f8c94f6ed13af158c
Source dataset
uspto-grants-1979_03
Patent number
US04144346

Linked notes

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