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

HRID 247622Notes

Reaction equation

HRID 247622 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 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. customremoved by azeotropic distillation
  4. concentrationThe mixture was concentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-efb37e2a71d94b7f84d0a78f6add92d3
Source dataset
uspto-grants-1987_11
Patent number
US04709052

Reaction notes

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