Tetrahydrofuran → 3-[(4-Chlorophenyl)sulfinyl]-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamide

HRID 1981806Notes

Reaction equation

HRID 1981806 reaction equation
[C:1](N1C=CN=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].C(N[N:16]([CH2:20][CH3:21])NCC)C.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH:31]2[CH2:35][CH2:34][NH:33][CH2:32]2)=[O:30])=[CH:25][CH:24]=1.O1CC[CH2:38][CH2:37]1>>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH:31]2[CH2:35][CH2:34][N:33]([C:1]([NH:3][CH2:7][CH2:6][N:16]([CH2:20][CH3:21])[CH2:37][CH3:38])=[O:2])[CH2:32]2)=[O:30])=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 682631,1'-CarbonyldiimidazoleHCID 136079753-[(4-Chlorophenyl)sulfinyl]pyrrolidineHCID 57254831N,N-diethylaminoethylamine

Product 1

HCID 136080073-[(4-Chlorophenyl)sulfinyl]-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamideYield 44.4%

Procedure

A solution of 4.37 g (0.027 mole) of 1,1'-carbonyldiimidazole and 2.96 g (0.0255 mole) of N,N-diethylaminoethylamine in 200 ml of tetrahydrofuran was stirred at room temperature for 45 min. A solution of 4.78 g (0.0209 mole) of 3-[(4-chlorophenyl)sulfinyl]pyrrolidine (free base) in tetrahydrofuran was added and the solution was refluxed for 16 hr. The solvent was removed in vacuo and the resulting oil was dissolved in methylene chloride. The methylene chloride solution was extracted with water and was dried over magnesium sulfate. The solvent was removed in vacuo. The solid residue was recrystallized from a mixture of methylene chloride, ether and hexane to give 3.45 g (44.4%) of white crystals, m.p. 127.5°-130° C.

Workup

  1. temperaturethe solution was refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting oil was dissolved in methylene chloride
  4. extractionThe methylene chloride solution was extracted with water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customThe solid residue was recrystallized from a mixture of methylene chloride, ether and hexane

Sources & evidence

ORD record
ord-e454335a49bf496ab278cda5bb3c620f
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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