Water → 1-Benzyl-4-diethylamino-3-pyrrolidinol

HRID 366889Notes

Reaction equation

HRID 366889 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH2:18].[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20]>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([N:21]([CH2:22][CH3:23])[CH2:19][CH3:20])[CH:10]([OH:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 8021DiethylamineHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 120440511-Benzyl-4-diethylamino-3-pyrrolidinolYield 74.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 12.0 g (0.12 mol) of 98% sulfuric acid, 15.0 g of water, and 60.0 g of acetone in a quartz round flask reactor, 45.6 g (0.20 mol) of (NH4)2S2O8 (ammonium peroxydisulfate produced by Mitsubishi Gas Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 5 days at room temperature with irradiation by 500 W Xe lamps (UXL-500D xenon lamp produced by Ushio). 21.9 g (0.3 mol) of diethylamine (produced by Katayama Chemical Industry Co., Ltd.) was continuously added to the reaction mixture and stirred for 5 hours under reflux. After completion, acetone and excess diethylamine were evaporated under reduced pressure, and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 18.4 g of 1-benzyl-4-diethylamino-3-pyrrolidinol (yield 73.9%) was obtained.

Workup

  1. customto react for 5 days at room temperature with irradiation by 500 W Xe lamps (UXL-500D xenon lamp produced by Ushio)
  2. stirringstirred for 5 hours
  3. temperatureunder reflux
  4. customAfter completion, acetone and excess diethylamine were evaporated under reduced pressure
  5. extractionextracted with toluene and water
  6. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-39761f47d9184fdc9960e200df23a7e3
Source dataset
uspto-grants-2000_10
Patent number
US06130338

Reaction notes

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