2-Nitroimidazole → 4-[3-(2-nitro-1H-imidazol-1-yl)propyl]-piperidinecarboxaldehyde

HRID 364712Notes

Reaction equation

HRID 364712 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O: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>[N+:1]([C:4]1[N:5]([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:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 107012-NitroimidazoleHCID 24758Sodium hydrideHCID 202397684-(3-Bromopropyl)-1-piperidinecarboxaldehyde

Product 1

HCID 202397414-[3-(2-nitro-1H-imidazol-1-yl)propyl]-piperidinecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The mixture of 2-nitroimidazole (11.3 g, 0.1M) and 50% by weight NaH in mineral oil (4.8 g, 0.1M) in dimethylformamide (50 ml) was stirred at room temperature for 1/2 hr. The solution of 4(3-bromo-propyl)-1-piperidine carboxaldehyde (23.4, 0.1M) in dimethylformamide (20 ml) was added to the above mixture and heated at 110° C. for 15 min. After the reaction, the solvent was removed in vacuo wand water (100 ml) was added and the mixture was extracted with ethylacetate (72×100 ml). The extracts, dried over Na2SO4, were concentrated and purified on silica gel columns, eluted with 5% by volume MeOH-95% by volume CH2Cl2 to give 4-[3-(2-nitro-1H-imidazol-1-yl)propyl]-piperidinecarboxaldehyde (22.8 g).

Workup

  1. temperatureheated at 110° C. for 15 min
  2. customAfter the reaction
  3. customthe solvent was removed in vacuo wand water (100 ml)
  4. additionwas added
  5. extractionthe mixture was extracted with ethylacetate (72×100 ml)
  6. dry with materialThe extracts, dried over Na2SO4
  7. concentrationwere concentrated
  8. custompurified on silica gel columns
  9. washeluted with 5% by volume MeOH-95% by volume CH2Cl2

Sources & evidence

ORD record
ord-d6017a7a67614bf0952c59b4ec5b8b4c
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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