Water → HCID 12044049, compound

HRID 366888Notes

Reaction equation

HRID 366888 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]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([NH:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[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 7504BenzylamineHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 12044049HCID 12044049, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

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). After evaporation of acetone under reduced pressure, continuously 32.1 g (0.3 mol) of benzylamine (produced by Katayama Chemical Industry Co., Ltd.) was added to the reaction mixture and stirred for 5 hours at 100° C. After completion, excess benzylamine was removed by distillation under reduced pressure, and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 20.9 g of 1-benzyl-4-benzylamino-3-pyrrolidinol (yield 74.0%) 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. additionwas added to the reaction mixture
  3. stirringstirred for 5 hours at 100° C
  4. customAfter completion, excess benzylamine was removed by distillation under reduced pressure
  5. extractionextracted with toluene and water
  6. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-548365991b5b4250974f7a6f5a483cba
Source dataset
uspto-grants-2000_10
Patent number
US06130338

Reaction notes

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