p-Toluidine → 1-p-Tolylaminocyclohexanecarbonitrile

HRID 244985Notes

Reaction equation

HRID 244985 reaction equation
[C-]#[N:2].[Na+].[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.[C:12]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(OCC)(=O)C>C(O)(=O)C>[CH3:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:14]2([C:13]#[N:2])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:12]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 10400Cycloheptanone

Product 1

HCID 598390991-p-TolylaminocyclohexanecarbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanide (0.147 g, 3 mmol) was added to a mixture of p-toluidine (0.214 g, 2 mmol) and cycloheptanone (0.337 g, 3 mmol) in acetic acid 90% (3 ml). The reaction mixture was stirred at room temperature for 12 h and then 20 ml of ethyl acetate was added. The organic layer was washed with water (3×10 ml), dried over magnesium sulfate and concentrated under vacuum to dryness to yield 1-(4-methylphenyl)aminocyclohexanenitrile, 10a (0.438 g, 1.92 mmol, 96%) as a brown solid.

Workup

  1. washThe organic layer was washed with water (3×10 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record
ord-9b265afe23d245f889e77b26a8d44617
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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