Benzylamine → 1-Benzyl-2,5-dihydropyrrole

HRID 366867

Reaction equation

HRID 366867 reaction equation
[CH3:1]/[CH:2]=[CH:3]\[CH3:4].[CH2:5]([NH2:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[CH2:5]([N:12]1[CH2:4][CH:3]=[CH:2][CH2:1]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 5287573cis-2-BUTENE

Product 1

HCID 5615061-Benzyl-2,5-dihydropyrroleYield 89.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 60.0 g of the cis-2-butene derivative solution prepared in Example 1 and 250 g of toluene in a round flask reactor, 171.7 g (1.6 mol) of benzylamine was added dropwise with stirring for 30 min. at ambient temperature. After 2 hours of stirring, the crystallized solid was removed by filtration; 42.0 g of 35% HCl (aq) was added to the filtrate, and then excess benzylamine hydrochloride was removed by filtration or extraction. After the solvent was evaporated under reduced pressure, 57.0 g of 1-benzyl-3-pyrroline (yield 89.5%) was obtained.

Workup

  1. stirringAfter 2 hours of stirring
  2. customthe crystallized solid was removed by filtration
  3. addition42.0 g of 35% HCl (aq) was added to the filtrate
  4. customexcess benzylamine hydrochloride was removed by filtration or extraction
  5. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b16b84cc9b0e4e38bfb16f8ea36576a5
Source dataset
uspto-grants-2000_10
Patent number
US06130338

Linked notes

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