Benzene → N-(Cyclohex-2-en-1-yl)cyclohexanimine

HRID 1461584Notes

Reaction equation

HRID 1461584 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:8]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C1C=CC=CC=1>[Cl-].[Zn+2].[Cl-].O>[C:1]1(=[N:7][CH:13]2[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 241BenzeneHCID 7967CyclohexanoneHCID 10931371HCID 10931371, compound

Product 1

HCID 13272647N-(Cyclohex-2-en-1-yl)cyclohexanimineYield 69.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-cyclohexenylamine (9.7 g, 0.1 mole), cyclohexanone (9.8 g, 0.1 mole), zinc chloride (0.16 g) and benzene (50 ml) was heated under reflux, and resulting water was removed by azeotropic distillation. The mixture was concentrated and distilled to obtain 12.4 g of N-cyclohexylidene-2-cyclohexenylamine [Compound (344)].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customwas removed by azeotropic distillation
  4. concentrationThe mixture was concentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-97d989fe4c36423e9ac8c2d0040265a9
Source dataset
uspto-grants-1991_12
Patent number
US05075488

Reaction notes

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