Imidazole → 4[3-(1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde

HRID 485799Notes

Reaction equation

HRID 485799 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]=[O:19])[CH2:14][CH2:13]1>CN(C)C=O>[N:1]1([CH2:9][CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH:18]=[O:19])[CH2:16][CH2:17]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 202397684-(3-Bromopropyl)-1-piperidinecarboxaldehyde

Product 1

HCID 137267384[3-(1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

The mixture of imidazole (0.7 g, 0.01M) and NaH (50% by weight in mineral oil, 0.9 g, 0.018M) in dimethylformamide (60 ml) was heated at 50° C. for 1/2 hr. and 4-(3-bromopropyl)-1-piperidinecarboxaldehyde (2.93 g, 0.0125M) in dimethylformamide (20 ml) was added. The reaction was heated at 50° C. for 4 hrs. After the reaction, the solvent was removed in vacuo, water was added and the product was extracted with CH2Cl2 (3×50 ml). The combined extracts, dried over Na2SO4, were stripped to dryness and purified on silica gel column eluted with 10% by volume methanol--90% by volume methylenechloride to give 4[3-(1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde as an oil (2.12 g, 96%).

Workup

  1. temperatureThe reaction was heated at 50° C. for 4 hrs
  2. customAfter the reaction
  3. customthe solvent was removed in vacuo, water
  4. additionwas added
  5. extractionthe product was extracted with CH2Cl2 (3×50 ml)
  6. dry with materialThe combined extracts, dried over Na2SO4
  7. custompurified on silica gel column
  8. washeluted with 10% by volume methanol--90% by volume methylenechloride

Sources & evidence

ORD record
ord-1f910d0d65774e6ba7661bac113d5eb4
Source dataset
uspto-grants-1985_08
Patent number
US04537969

Reaction notes

Loading…