N,N-Diethyl-1,3-propanediamine → HCID 20218052, compound

HRID 236111Notes

Reaction equation

HRID 236111 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 20218052HCID 20218052, compound

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-da42ed97589d46edbf8cba552c81120c
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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