Sodium Hydroxide → HCID 131714712, compound

HRID 236090Notes

Reaction equation

HRID 236090 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH:10]2[CH2:14][CH2:13][N:12](CC3C=CC=CC=3)[CH2:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:22]C(OC1C=CC=CC=1)=[O:24].[OH-].[Na+]>C(Cl)Cl.Br>[OH2:24].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[ClH:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 13607941HCID 13607941, compound

Product 1

HCID 131714712HCID 131714712, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 18.90 g (0.0561 mole) of 3-[(3,4-dichlorophenyl)thio]-1-(phenylmethyl)pyrrolidine (free base) and 11.0 g (0.070 mole) of phenyl chloroformate in 800 ml of methylene chloride was stirred at room temperature for 3 hr. The methylene chloride solution was extracted first with dilute sulfuric acid followed by dilute sodium hydroxide, dried and evaporated in vacuo to give an oil. The oil was suspended in 300 ml of 48% hydrobromic acid and the mixture refluxed overnight. The reaction mixture was poured over ice and the mixture made basic with sodium hydroxide. The basic mixture was extracted with methylene chloride and the methylene chloride layer separated and dried over magnesium sulfate and evaporated in vacuo to give an oil, the free base of the title compound. The hydrochloride salt was prepared in methanol with ethereal hydrogen chloride and recrystallized from methanol diethyl ether to give a white crystalline salt. On drying under high vacuum at 80° C. the solid melted. On cooling, the melt formed a gloss, the monohydrochloride, hemihydrate.

Workup

  1. extractionThe methylene chloride solution was extracted first with dilute sulfuric acid
  2. customdried
  3. customevaporated in vacuo
  4. customto give an oil
  5. temperaturethe mixture refluxed overnight
  6. additionThe reaction mixture was poured over ice
  7. extractionThe basic mixture was extracted with methylene chloride
  8. customthe methylene chloride layer separated
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customto give an oil

Sources & evidence

ORD record
ord-321263409081412288414c787e7fadee
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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