Toluene → 1-{2-[(4-Oxo-2,5-cyclohexadien-1-ylidene)amino]benzoyl}piperidine

HRID 464790Notes

Reaction equation

HRID 464790 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=2[C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1>C(O)C>[O:1]=[C:2]1[CH:7]=[CH:6][C:5](=[N:8][C:9]2[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=2[C:11]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)=[O:12])[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 1140TolueneHCID 135056311-[2-(4-Hydroxyphenylamino)benzoyl]piperidine

Product 1

HCID 135056741-{2-[(4-Oxo-2,5-cyclohexadien-1-ylidene)amino]benzoyl}piperidineYield 35.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.9 g (0.03 mole) 1-[2-(4-hydroxyphenylamino)benzoyl]piperidine, 6.4 g (0.03 mole) of mercuric oxide, 80 ml of toluene and 20 ml of ethanol was heated at reflux for three hours. The reaction mixture was filtered through an alumina column and eluted with ethyl acetate. The solvent was removed in vacuo and the residue subjected to high pressure liquid chromatography, eluting with 20% ethyl acetate in hexane. The resulting 5.4 g of oil was partitioned between water and ether, the ether fraction dried over anhydrous sodium sulfate and concentrated, and the residue recrystallized from hexane to give 3.1 g of 1-{2-[(4-oxo-2,5-cyclohexadien-1-ylidene)amino]benzoyl}piperidine, orange powder, m.p. 74°-76° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. filtrationThe reaction mixture was filtered through an alumina column
  4. washeluted with ethyl acetate
  5. customThe solvent was removed in vacuo
  6. washeluting with 20% ethyl acetate in hexane
  7. customThe resulting 5.4 g of oil was partitioned between water and ether
  8. dry with materialthe ether fraction dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customthe residue recrystallized from hexane

Sources & evidence

ORD record
ord-9550a04eb3f44785811f1813eb071577
Source dataset
uspto-grants-1985_10
Patent number
US04549016

Reaction notes

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