Piperidine → N-(2-chloroethyl)benzenesulfonamide

HRID 838795Notes

Reaction equation

HRID 838795 reaction equation
O[CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].N1CCCCC1.S(Cl)([Cl:23])(=O)=O>C(Cl)(Cl)(Cl)Cl>[Cl:23][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 24648Sulfuryl chlorideHCID 1722145N-(2-hydroxyethyl)benzenesulfonamide

Product 1

HCID 4562550N-(2-chloroethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideCatalyst

Procedure

40.2 g. of N-(β-hydroxyethyl)-benzene sulfonamide was slurried in 100 ml. of carbon tetrachloride containing 5 drops of piperidine. Then, 47.6 g. of sulfonyl chloride was added over 10 minutes, keeping the temperature at 20°-25° C. during the addition. The reaction was completed by heating on a steam bath for one hour. The mixture was concentrated on the steam bath, dissolved in benzene and washed twice with dilute aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and the benzene evaporated on the steam bath with air. The product was crystallized from benzene cyclohexane to yield 28.0 g. of product, m.p. 58°-62° C.

Workup

  1. customat 20°-25° C.
  2. additionduring the addition
  3. temperatureby heating on a steam bath for one hour
  4. concentrationThe mixture was concentrated on the steam bath
  5. dissolutiondissolved in benzene
  6. washwashed twice with dilute aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe benzene evaporated on the steam bath with air
  10. customThe product was crystallized from benzene cyclohexane
  11. customto yield 28.0 g

Sources & evidence

ORD record
ord-af217c8a116d4497901a09f40495c96c
Source dataset
uspto-grants-1978_06
Patent number
US04093445

Reaction notes

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