Toluene → Ethyl 4-[(4-chlorophenyl)imino]-1-piperidinecarboxylate

HRID 26733

Reaction equation

HRID 26733 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.CC1C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 78124-ChloroanilineHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

HCID 14665236Ethyl 4-[(4-chlorophenyl)imino]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 171.2 parts of ethyl 4-oxo-1-piperidinecarboxylate, 159.5 parts of 4-chlorobenzeneamine, 1520 parts of anhydrous methylbenzene and a few crystals of 4-methylbenzenesulfonic acid is stirred and refluxed for 7 hours. (The reaction vessel is provided with a reflux-condensor and water-separator). The methylbenzene is evaporated and the oily residue is distilled in vacuo, yielding 192 parts of oily ethyl 4-[(4-chlorophenyl)imino]-1-piperidine-carboxylate; bp. 171°-176° C. at 0.4 mm. pressure.

Workup

  1. temperaturerefluxed for 7 hours
  2. custom(The reaction vessel is provided with
  3. temperaturea reflux-condensor
  4. customThe methylbenzene is evaporated
  5. distillationthe oily residue is distilled in vacuo

Sources & evidence

ORD record
ord-d57b5d7ea41b4259acc2bd37a7ee7e13
Source dataset
uspto-grants-1979_04
Patent number
US04151286

Linked notes

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