Phenyl chloroformate → 3-((4-Chlorophenyl)sulfonyl)pyrrolidine hydrochloride

HRID 236087Notes

Reaction equation

HRID 236087 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC(OC1C=CC=CC=1)=O>C(Cl)Cl.S(=O)(=O)(O)O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:15][CH2:14][NH:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 136079393-[(4-Chlorophenyl)sulfonyl]-1-(phenylmethyl)pyrrolidine

Product 1

HCID 202178543-((4-Chlorophenyl)sulfonyl)pyrrolidine hydrochloride

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 8.31 g (0.0248 mole) of 3-[(4-chlorophenyl)sulfonyl]-1-(phenylmethyl)pyrrolidine (free base) and 7.1 g (0.0455 mole) of phenyl chloroformate in 300 ml of methylene chloride was stirred at room temperature for 20 hr. The solution was extracted several times with dilute aqueous sodium hydroxide solution and the organic layer was separated and dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. The oil was suspended in 300 ml of 60% sulfuric acid and the mixture poured over ice. The resulting acidic mixture was extracted with methylene chloride and the methylene chloride layer was discarded. The acidic aqueous layer was made basic with 50% sodium hydroxide solution and extracted with methylene chloride. The methylene chloride extract of the basic solution was dried over magnesium sulfate and the solvent removed in vacuo to give an oil, the free base of the title compound. The hydrochloride salt was prepared using ethereal hydrogen chloride added to a methanol solution of the free base and recrystallized from methyl alcohol-diethyl ether to give 4.11 g (58.9%) of white crystalline solid, m.p. 202°-203° C.

Workup

  1. extractionThe solution was extracted several times with dilute aqueous sodium hydroxide solution
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customto give an oil
  6. additionthe mixture poured over ice
  7. extractionThe resulting acidic mixture was extracted with methylene chloride
  8. extractionextracted with methylene chloride
  9. extractionThe methylene chloride extract of the basic solution
  10. dry with materialwas dried over magnesium sulfate
  11. customthe solvent removed in vacuo
  12. customto give an oil

Sources & evidence

ORD record
ord-c02b6bfdebf8497182f345e04e5c351e
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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