Dichloromethane → N-[2-[(4-Fluorophenyl)sulfonyl]ethyl]-2-propanamine hydrochloride

HRID 4197Notes

Reaction equation

HRID 4197 reaction equation
C1(OC(=O)[N:9]([CH2:13][CH2:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:10]([CH3:12])[CH3:11])C=CC=CC=1.[OH-].[Na+].C(Cl)[Cl:29]>Br.CO>[ClH:29].[F:24][C:21]1[CH:20]=[CH:19][C:18]([S:15]([CH2:14][CH2:13][NH:9][CH:10]([CH3:12])[CH3:11])(=[O:16])=[O:17])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 13655161N-[2-[(4-fluorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester

Product 1

HCID 13655062N-[2-[(4-Fluorophenyl)sulfonyl]ethyl]-2-propanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 887MethanolSolvent

Procedure

A solution of 60.25 g (0.165 mole) of N-[2-[(4-fluorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester in 400 ml of 48% HBr was heated at reflux for 8 hr. The reaction mixture was cooled with ice and made alkaline with 50% sodium hydroxide. The aqueous phase was extracted with chloroform. The chloroform layer was extracted with sodium hydroxide. Evaporation of the chloroform layer gave an oil residue. The oil was dissolved in methylene chloride and the solution extracted with 1N sulfuric acid. The acidic layer was made alkaline with a mixture of ice and 50% sodium hydroxide solution and extracted with chloroform. Removal of chloroform gave an oil, the free base of the title compound, which was dissolved in methanol and reacted with ethereal hydrogen chloride to give the hydrochloride salt. On recrystallization from methanol-diethyl ether a white crystalline product; m.p. 168°-169° C. in 31.1% yield was obtained.

Workup

  1. temperatureat reflux for 8 hr
  2. temperatureThe reaction mixture was cooled with ice
  3. extractionThe aqueous phase was extracted with chloroform
  4. extractionThe chloroform layer was extracted with sodium hydroxide
  5. customEvaporation of the chloroform layer
  6. customgave an oil residue
  7. extractionthe solution extracted with 1N sulfuric acid
  8. additionwith a mixture of ice and 50% sodium hydroxide solution
  9. extractionextracted with chloroform
  10. customRemoval of chloroform
  11. customgave an oil

Sources & evidence

ORD record
ord-b9c7f498abcf44048992767b6acc95b5
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Reaction notes

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