4-(4-Chlorobenzene-1-sulfonyl)piperidine--hydrogen chloride (1/1) → HCID 18538477, compound

HRID 236099Notes

Reaction equation

HRID 236099 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:18][O-:19].[Na+]>CS(C)=O>[ClH:2].[CH3:18][O:19][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 27610714-(4-Chlorobenzene-1-sulfonyl)piperidine--hydrogen chloride (1/1)HCID 10942334Sodium Methoxide

Product 1

HCID 18538477HCID 18538477, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1.12 g (0.0038 mole) of 4-[(4-chlorophenyl)sulfonyl]piperidine monohydrochloride and 0.0152 mole of sodium methoxide in 60 ml of dimethylsulfoxide was heated at 90° C. for 2 hrs. The reaction mixture was quenched in water and diluted mixture was extracted with methylene chloride. The methylene chloride phase was dried over sodium sulfate and the solvent was removed on the rotary evaporator. The residue (the free base of the title compound) was dissolved in methanol and the solution was treated with an excess of ethereal hydrogen chloride. The resulting hydrochloride salt was recrystallized from methanol-diethyl ether to give white crystalline solid, m.p. 275°-276° C.

Workup

  1. customThe reaction mixture was quenched in water
  2. additiondiluted mixture
  3. extractionwas extracted with methylene chloride
  4. dry with materialThe methylene chloride phase was dried over sodium sulfate
  5. customthe solvent was removed on the rotary evaporator
  6. dissolutionThe residue (the free base of the title compound) was dissolved in methanol
  7. additionthe solution was treated with an excess of ethereal hydrogen chloride
  8. customThe resulting hydrochloride salt was recrystallized from methanol-diethyl ether
  9. customto give white crystalline solid, m.p. 275°-276° C.

Sources & evidence

ORD record
ord-9bbda542e6bb41a292f344a929044142
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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