Butanal → HCID 14514400, compound

HRID 1493229Notes

Reaction equation

HRID 1493229 reaction equation
BrC1C=CN=CC=1.[Li].C(=O)CCC.S(Cl)(Cl)=O.Cl[CH:19]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22].[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1.[H-].[Na+].Cl>CN(C)C=O>[N:29]1([CH:19]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH2:20][CH2:21][CH3:22])[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

10

Reactant 8

HCID 261ButanalHCID 313Hydrochloric AcidHCID 795ImidazoleHCID 142684-BromopyridineHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 3028194LithiumHCID 19831109HCID 19831109, compound2×

Product 1

HCID 14514400HCID 14514400, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The initial material, 4-(1-chlorobutyl)-pyridine, necessary for this reaction is obtained by the following reaction sequence. Commercial 4-bromo-pyridine is converted, by halometal exchange, into the corresponding 4-lithium-pyridine compound. This lithium compound is converted, with butyraldehyde, into the corresponding secondary alcohol. The alcohol is then converted by reaction with thionyl chloride into 4-(1-chlorobutyl)pyridine. 0.68 g of imidazole is dissolved in 5 ml of dimethylformamide, 0.3 g of sodium hydride (80%) is added and stirred for 10 minutes at room temperature. A solution of 3.87 g of 4-(1-chlorobutyl)-pyridine in 4 ml of dimethylformamide is added to this solution and stirred for 24 hours at room temperature. Then it is poured into 100 ml of 10% hydrochloric acid and extracted with ethyl acetate. The aqueous phase is made alkaline with sodium hydroxide solution (pH 13) and extracted with methylene chloride. The methylene chloride solution is concentrated by evaporation in a vacuum and the residue is distilled on a bulb tube, boiling point: 170°-190° C./0.04 mbar. 0.3 g of 4-[1-(1-imidazolyl)-butyl]-pyridine is obtained.

Workup

  1. stirringstirred for 24 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. extractionextracted with methylene chloride
  4. concentrationThe methylene chloride solution is concentrated by evaporation in a vacuum
  5. distillationthe residue is distilled on a bulb tube

Sources & evidence

ORD record
ord-2dc4d463732f4647accf0b0a8a4a0cef
Source dataset
uspto-grants-1991_06
Patent number
US05021434

Reaction notes

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