N,N-Diethyl-1,3-propanediamine → N-[3-(Diethylamino)propyl]-3-(phenylsulfonyl)-1-pyrrolidinecarboxamide Monohydrate

HRID 1981809Notes

Reaction equation

HRID 1981809 reaction equation
[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][CH2:6][NH2:7])[CH3:2].[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11].[C:22]1([S:28]([CH:31]2[CH2:35][CH2:34][NH:33][CH2:32]2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[OH2:11].[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][CH2:6][NH:7][C:10]([N:33]1[CH2:34][CH2:35][CH:31]([S:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:30])=[O:29])[CH2:32]1)=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 682631,1'-CarbonyldiimidazoleHCID 36142033-(Phenylsulfonyl)pyrrolidine

Product 1

HCID 20218052N-[3-(Diethylamino)propyl]-3-(phenylsulfonyl)-1-pyrrolidinecarboxamide Monohydrate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.95 g (0.38 mole) of 3-diethylaminopropylamine and 6.50 g (0.040 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 7.08 g (0.0336 mole) of 3-(phenylsulfonyl)pyrrolidine (free base) in 100 ml of tetrahydrofuran was added and the mixture was refluxed overnight. The tetrahydrofuran was removed in vacuo and the residue was partitioned between methylene chloride and water. The methylene chloride phase was dried over magnesium sulfate and the solvent was removed in vacuo to give the product as an oil.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe tetrahydrofuran was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and water
  4. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-12c0bdeefcb04e12a98154386324c8f8
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

Loading…