Imidazole → HCID 18928720, compound

HRID 1599475Notes

Reaction equation

HRID 1599475 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:26])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][CH2:12]1.[OH-].[Na+]>O1CCCC1.O>[N:1]1([CH2:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:26])[CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:15][CH2:16]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 18928715HCID 18928715, compound

Product 1

HCID 18928720HCID 18928720, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of imidazole (1.4 g) in dry tetrahydrofuran (20 ml) was added dropwise with stirring to a mixture of sodium hydride (0.8 g, 60% dispersion in mineral oil) in tetrahydrofuran (20 ml) under nitrogen. The mixture was stirred at 20° C. for 3 hours and then a solution of the product from Example 42 (5.6 g) in dry tetrahydrofuran (50 ml) was added dropwise with stirring. The mixture was heated under reflux for 9 hours and then cooled to 20° C. Water (50 ml) was added and the solution stirred for 10 minutes. The mixture was basified with dilute sodium hydroxide solution and extracted with dichloromethane. The combined dichloromethane extracts were washed (water), dried and filtered before evaporation to give 4-[2-(imidazol-1-yl)ethyl]-1-(3-phenylpropionyl)piperidine as an oil.

Workup

  1. stirringwith stirring
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 9 hours
  4. temperaturecooled to 20° C
  5. stirringthe solution stirred for 10 minutes
  6. extractionextracted with dichloromethane
  7. washThe combined dichloromethane extracts were washed (water)
  8. customdried
  9. filtrationfiltered before evaporation

Sources & evidence

ORD record
ord-538942c371ef481b82b4744a5dfd94e8
Source dataset
uspto-grants-1998_04
Patent number
US05741800

Reaction notes

Loading…