Benzaldehyde → Hydrocarbostyril

HRID 1708281Notes

Reaction equation

HRID 1708281 reaction equation
NCCCOC1C=CC(C(N2CCC([N:18]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21][C:19]3=[O:20])CC2)=O)=CC=1.C(=O)C1C=CC=CC=1.B.[Na]>CO>[NH:18]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][C:19]1=[O:20]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14969544HCID 14969544, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 64796HydrocarbostyrilYield 201.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-{1-[4-(3-aminopropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1.4 g), benzaldehyde (0.42 ml) and methanol (15 ml) is stirred at room temperature for 3 hours and cooled with ice. Thereto is added sodium boron hydride (0.21 g) and the mixture is stirred under ice cooling for 2 hours and then allowed to stand a room temperature overnight. The solvent is distilled off and water is added to the resulting residue and the mixture is extracted with ethyl acetate. The extract is washed successively with saturated sodium hydrogen carbonate, water and saline solution, dried with sodium sulfate and then the solvent is distilled off. The resulting residue is purified by silica gel column chromatography (solvent: methanol:dichloromethane=1:100) to give 1-{1-[4-benzylaminopropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1.02 g).

Workup

  1. temperaturecooled with ice
  2. stirringthe mixture is stirred under ice cooling for 2 hours
  3. waitto stand a room temperature overnight
  4. distillationThe solvent is distilled off
  5. additionwater is added to the resulting residue
  6. extractionthe mixture is extracted with ethyl acetate
  7. washThe extract is washed successively with saturated sodium hydrogen carbonate, water and saline solution
  8. dry with materialdried with sodium sulfate
  9. distillationthe solvent is distilled off
  10. customThe resulting residue is purified by silica gel column chromatography (solvent: methanol:dichloromethane=1:100)

Sources & evidence

ORD record
ord-40a4a2669730426081877f9543ff6048
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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