HCID 14500631, compound → HCID 14500659, compound

HRID 1761599Notes

Reaction equation

HRID 1761599 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([NH2:17])=[O:16])[CH:9]=1>C(O)(=O)C>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([NH2:17])=[O:16])[CH:9]=1

Participants

3

Reactant 1

HCID 14500631HCID 14500631, compound

Product 1

HCID 14500659HCID 14500659, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2 g (8.7 mmol) of 1-methyl-2-(3-ureidobenzyl)pyrrole, prepared, for example, as described in Preparation 3E, in 80 ml of glacial acetic acid was hydrogenated at 45 p.s.i. in the presence of 1.5 g of 5% rodium on activated alumina as catalyst, for 1 hour. The catalyst was then separated by filtration and the filtrate evaporated in vacuo. The residue was suspended in 100 ml of methylene chloride and 20 ml of ammonium hydroxide was added. The mixture was dried over sodium sulfate and evaporated under reduced pressure. Crystallization of the residue from acetone-ether afforded 870 mg (43%) of the title compound, 1-methyl-2-(3'-ureidobenzyl)pyrrolidine. M.P. 133°-135° C. (ether)

Workup

  1. customThe catalyst was then separated by filtration
  2. customthe filtrate evaporated in vacuo
  3. addition20 ml of ammonium hydroxide was added
  4. dry with materialThe mixture was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customCrystallization of the residue from acetone-ether

Sources & evidence

ORD record
ord-b27fad3d5b0c466d8c021ae1791cbbd8
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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