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

HRID 1981807Notes

Reaction equation

HRID 1981807 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:32]2[CH2:36][CH2:35][NH:34][CH2:33]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1.O1CC[CH2:39][CH2:38]1>>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH:32]2[CH2:36][CH2:35][N:34]([C:1]([NH:3][CH2:7][CH2:6][N:16]([CH2:20][CH3:21])[CH2:38][CH3:39])=[O:2])[CH2:33]2)(=[O:30])=[O:31])=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 682631,1'-CarbonyldiimidazoleHCID 136079763-[(4-Chlorophenyl)sulfonyl]pyrrolidineHCID 57254831N,N-diethylaminoethylamine

Product 1

HCID 136080083-[(4-Chlorophenyl)sulfonyl]-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamideYield 46.7%

Procedure

A solution of 4.93 g (0.0304 mole) of 1,1'-carbonyldiimidazole and 3.36 g (0.029 mole) of N,N-diethylaminoethylamine in 200 ml of tetrahydrofuran was stirred for 40 min at room temperature. A solution of 5.78 g (0.0236 mole) of 3-[(4-chlorophenyl)sulfonyl]pyrrolidine (free base) in tetrahydrofuran was added and the solution was refluxed overnight. The solvent was removed in vacuo and the resulting oil was dissolved in methylene chloride. The solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil residue. The residue was crystallized from a mixture of methanol, ether and hexane to give 4.28 g (46.7%) of white crystals, m.p. 86°-87.5° C.

Workup

  1. temperaturethe solution was refluxed overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting oil was dissolved in methylene chloride
  4. extractionThe solution was extracted with several portions of water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give an oil residue
  8. customThe residue was crystallized from a mixture of methanol, ether and hexane

Sources & evidence

ORD record
ord-b659a221b55e4eb1928caabd42358eec
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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