Hydrochloric Acid → HCID 14500669, compound

HRID 1761602Notes

Reaction equation

HRID 1761602 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18]([NH2:20])=[O:19])[CH:12]=1)[CH2:2][CH2:3][CH3:4].Cl>O.CO>[CH2:1]([N:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18]([NH2:20])=[O:19])[CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14500646HCID 14500646, compound

Product 1

HCID 14500669HCID 14500669, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A suspension of 1.25 g (4.6 mmol) of 1-butyl-2-(3'-ureidobenzyl)pyrrole, prepared, for example, as described in Preparation 6D, in a mixture of 75 ml of water, 75 ml of methanol and 10 ml of a 1N solution of hydrochloric acid in methanol, was hydrogenated at 45 p.s.i. in the presence of 1 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 aqueous residue was treated with concentrated ammonium hydroxide until an alkaline pH was obtained, and the product extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water (2×50 ml), dried and evaporated under reduced pressure. The residue was purified by column chromatography on 100 g of silica gel, using an (80:20) mixture of methylene chloride-[chloroform-methanol-ammonium hydroxide (60:10:1)] as the eluting system, thus obtaining 550 mg (44%) of the title compound, 1-butyl-2-(3'-ureidobenzyl)pyrrolidine, which was recrystallized from acetone-hexane. M.P. 80°-83° C.

Workup

  1. customThe catalyst was then separated by filtration
  2. customthe filtrate evaporated in vacuo
  3. additionThe aqueous residue was treated with concentrated ammonium hydroxide until an alkaline pH
  4. customwas obtained
  5. extractionthe product extracted with ethyl acetate (3×50 ml)
  6. washThe combined extracts were washed with water (2×50 ml)
  7. customdried
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on 100 g of silica gel
  10. additionan (80:20) mixture of methylene chloride-[chloroform-methanol-ammonium hydroxide (60:10:1)] as the eluting system

Sources & evidence

ORD record
ord-0b05e2499d8f4954ab5b1d187f187274
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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