Sodium hydride → 4-[3-(2-ethyl-4-methyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde

HRID 364711Notes

Reaction equation

HRID 364711 reaction equation
[CH2:1]([C:3]1[NH:4][CH:5]=[C:6]([CH3:8])[N:7]=1)[CH3:2].[H-].[Na+].Br[CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH:21]=[O:22])[CH2:17][CH2:16]1>CN(C)C=O>[CH2:1]([C:3]1[N:4]([CH2:12][CH2:13][CH2:14][CH:15]2[CH2:16][CH2:17][N:18]([CH:21]=[O:22])[CH2:19][CH2:20]2)[CH:5]=[C:6]([CH3:8])[N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 202397684-(3-Bromopropyl)-1-piperidinecarboxaldehydeHCID 178437635HCID 178437635, compound

Product 1

HCID 202397584-[3-(2-ethyl-4-methyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehydeYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Ethyl-4-methyl-1H-imidazole (3.3 g, 30 mM) and sodium hydride (50% by weight in mineral oil, 80 mM) in dimethylformamide (20 ml) was heated at 50° C. for 1/2 hour. The solution of 4-(3-bromopropyl)-1-piperidinecarboxaldehyde (7 g, 30 mM) in dimethylformamide (20 ml) was added at 50° C. and stirred at that temperature for 4 hours. After the reaction, solvent was removed in vacuo and water (100 ml) was added and then extracted with ethyl acetate (2×100 ml). The extracts, dried over Na2SO4, was stripped to dryness and purified on silica gel column, eluted with 2% by volume MeOH, 98% by volume CH2Cl2, to give 4-[3-(2-ethyl-4-methyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde as an oil (4.04 g, 51% yield).

Workup

  1. customAfter the reaction, solvent
  2. customwas removed in vacuo and water (100 ml)
  3. additionwas added
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. dry with materialThe extracts, dried over Na2SO4
  6. custompurified on silica gel column
  7. washeluted with 2% by volume MeOH, 98% by volume CH2Cl2

Sources & evidence

ORD record
ord-6b39da5a8ea74bf8af954c9d50f0c9f7
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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