Diethyl Ether → 4-{N-[alpha-(4-Methyl-phenyl)-2-piperidino-benzyl]-aminocarbonylmethyl}-benzaldehyde

HRID 648650Notes

Reaction equation

HRID 648650 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][C:22]([CH2:24][C:25]2[CH:32]=[CH:31][C:28]([CH2:29][OH:30])=[CH:27][CH:26]=2)=[O:23])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][C:22]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([CH:29]=[O:30])=[CH:31][CH:32]=2)=[O:23])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 54244181HCID 54244181, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 201452794-{N-[alpha-(4-Methyl-phenyl)-2-piperidino-benzyl]-aminocarbonylmethyl}-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

One-half gram (1.2 m mol) of 4-{N-[α-(4-methyl-phenyl)-2-piperidino-benzyl]-aminocarbonylmethyl}-benzyl alcohol was added to a suspension of 0.4 gm (1.5 m mol) of pyridinium chlorochromate in 2 ml of chloroform. After 12 hours at ambient temperature, ether was added, the mixture was filtered, and the concentrated filtrate was purified by column chromatography on silica gel [eluant: toluene/ethyl acetate (5:1)].

Workup

  1. filtrationthe mixture was filtered
  2. customthe concentrated filtrate was purified by column chromatography on silica gel [eluant: toluene/ethyl acetate (5:1)]

Sources & evidence

ORD record
ord-f71fb74468af43238755c75397476518
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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