(Z)-1-(imidazol-2-yl)-1-[(4-methyl)phenyl]-3-(1-pyrrolidyl)prop-1-ene → 1-(Imidazol-2-yl)-1-(4-methylphenyl)-3-(1-pyrrolidyl)propane

HRID 2285737Notes

Reaction equation

HRID 2285737 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1/[C:6](/[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=[CH:7]\[CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>C(O)C.[Pd]=O>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1)[CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 13019456(Z)-1-(imidazol-2-yl)-1-[(4-methyl)phenyl]-3-(1-pyrrolidyl)prop-1-ene

Product 1

HCID 130194581-(Imidazol-2-yl)-1-(4-methylphenyl)-3-(1-pyrrolidyl)propaneYield 67.2%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent

Procedure

A solution of (Z)-1-(imidazol-2-yl)-1-[(4-methyl)phenyl]-3-(1-pyrrolidyl)prop-1-ene (0.31 g) in absolute ethanol (40 ml) was hydrogenated over 10% palladium oxide on charcoal (0.03 g). Absorption of hydrogen was complete after 3 h. The catalyst was removed by filtration and the filtrate concentrated to a colourless oil which solidified. Recrystallisation from isopropyl acetate afforded the title compound as pale pink crystals m.p. 125°-127° (0.21 g); τ(CDCl3)2.92(4H,s,aromatic),3.09(2H,s,imidazole), ##STR42## 7.68(3H,s,--CH3), ##STR43##

Workup

  1. customAbsorption of hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated to a colourless oil which
  4. customRecrystallisation from isopropyl acetate

Sources & evidence

ORD record
ord-09fb19b8120e462b8d219c28f8049f99
Source dataset
uspto-grants-1982_04
Patent number
US04324792

Reaction notes

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