89573-00-2 → 4-{N-[alpha-(4-Methyl-phenyl)-2-piperidino-benzyl]-aminocarbonylmethyl}-benzaldehyde

HRID 648649Notes

Reaction equation

HRID 648649 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:33]=[CH:32][C:28]([C:29](O)=[O: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>O1CCCC1>[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:32][CH:33]=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

3

Reactant 1

HCID 302146289573-00-2

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
170 °C

Procedure

Quantities of 8.85 gm (20 m mol) of 4-{N-[α-(4-Methylphenyl)-2-piperidino-benzyl]-aminocarbonylmethyl}-benzoic acid and 3.25 gm (20 m mol) of N,N'-carbonyldiimidazole were refluxed in 100 ml of absolute tetrahydrofuran for two hours. Then, the mixture was concentrated by evaporation, and, after addition of 50 ml of pyridine and 3.7 gm (20 m mol) of 4-toluene-sulphonic acid hydrazide, the mixture was refluxed for a further two hours. The mixture was then poured onto ice water and subjected to suction filtration, and the precipitate was dried. The resulting crude toluene-sulphonic acid hydrazide of the carboxylic acid used was mixed with 20 gm of anhydrous sodium carbonate and heated to 170° C. in 50 ml of ethylene glycol for two hours. Then, it was added to water and extracted with chloroform. The concentrated extracts were purified by column chromatography on silica gel by use of toluene/ethyl acetate (5:1) as eluant.

Workup

  1. concentrationThen, the mixture was concentrated by evaporation
  2. additionafter addition of 50 ml of pyridine and 3.7 gm (20 m mol) of 4-toluene-sulphonic acid hydrazide
  3. temperaturethe mixture was refluxed for a further two hours
  4. additionThe mixture was then poured onto ice water
  5. filtrationsubjected to suction filtration
  6. customthe precipitate was dried
  7. additionThe resulting crude toluene-sulphonic acid hydrazide of the carboxylic acid used was mixed with 20 gm of anhydrous sodium carbonate
  8. additionThen, it was added to water
  9. extractionextracted with chloroform
  10. customThe concentrated extracts were purified by column chromatography on silica gel by use of toluene/ethyl acetate (5:1) as eluant

Sources & evidence

ORD record
ord-8f66b23d75554ca1892d52cdec9edc44
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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