Toluene → HCID 13094166, compound

HRID 1164363Notes

Reaction equation

HRID 1164363 reaction equation
O=[C:2]1[CH2:7][CH2:6][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)([C:8]#[N:9])[CH2:4][CH2:3]1.[C:16]1([C:22]2([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC1C=CC(S(O)(=O)=O)=CC=1.CC1C=CC=CC=1>O>[C:8]([C:5]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:6][CH2:7][C:2]([N:25]2[CH2:24][CH2:23][C:22]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26]2)=[CH:3][CH2:4]1)#[N:9]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 32414NormeperidineHCID 107505374-OXO-1-(2-PYRIDINYL)CYCLOHEXANECARBONITRILE

Product 1

HCID 13094166HCID 13094166, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.5 parts of 4-oxo-1-(2-pyridinyl)cyclohexanecarbonitrile, 5.2 parts of ethyl 4-phenyl-4-piperidinecarboxylate, 1 part of 4-methylbenzenesulfonic acid and 225 parts of methylbenzene is stirred and refluxed overnight using a water-separator. The reaction mixture is evaporated and the residue is crystallized from 2-propanol, yielding 4.5 parts (45%) of ethyl 1-[4-cyano-4-(2-pyridinyl)-1-cyclohexeneyl]-4-phenyl-4-piperidinecarboxylate; mp. 160° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. customthe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-2b840e85555e46f5945acf1f8a7b1e55
Source dataset
uspto-grants-1983_01
Patent number
US04369184

Reaction notes

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