HCID 14500636, compound → HCID 14500661, compound

HRID 1761600Notes

Reaction equation

HRID 1761600 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([NH2:18])=[O:17])[CH:10]=1)[CH3:2]>C(O)(=O)C>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([NH2:18])=[O:17])[CH:10]=1)[CH3:2]

Participants

3

Reactant 1

HCID 14500636HCID 14500636, compound

Product 1

HCID 14500661HCID 14500661, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4 g (20 mmol) of 1-ethyl-2-(3'-ureidobenzyl)pyrrole, prepared, for example, as described in Preparation 4D, in 100 ml of glacial acetic acid was hydrogenated at 45 p.s.i. in the presence of 3 g of 5% rodium on activated alumina as catalyst, for 75 minutes. 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 concentrated ammonium hydroxide was added. The mixture was dried over sodium sulfate and evaporated under reduced pressure. The residue was crystallized from ethyl acetate-hexane, to yield 2.26 g (46%) of the title compound, 1-ethyl-2-(3'-ureidobenzyl)pyrrolidine. M.P. 114°-116°

Workup

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

Sources & evidence

ORD record
ord-f2488b0007874dedab952b4722c779b0
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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