Aniline → 1-Phenylamino-cyclohexanecarbonitrile

HRID 1894849Notes

Reaction equation

HRID 1894849 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C[Si]([C:19]#[N:20])(C)C>C(O)(=O)C>[C:2]1([NH:1][C:8]2([C:19]#[N:20])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115Aniline2×HCID 7967Cyclohexanone2×HCID 82115Trimethylsilyl cyanide

Product 1

HCID 2910301-Phenylamino-cyclohexanecarbonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.4 ml (15.3 mmol) of aniline (starting product 1) are added to a solution of 1.3 ml (12.5 mmol) of cyclohexanone (starting product 2) in 20 ml of acetic acid at 0° C. The solution is stirred for a time and 1.9 ml (14.2 mmol) of trimethylsilyl cyanide are added. The reaction medium is stirred for one night at room temperature. It is then poured gently into an ice-cold ammonium hydroxide solution until the pH is basic and extracted with dichloromethane. The organic phases are collected and washed with water. They are dried over sodium sulfate. The residue is precipitated in dichloromethane and heptane. The solid is filtered and dried. 2.2 g of 1-phenylaminocyclohexanecarbonitrile are obtained in the form of a whitish solid. M.p.=67-9° C., yield=88%.

Workup

  1. additionare added
  2. extractionextracted with dichloromethane
  3. customThe organic phases are collected
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customThe residue is precipitated in dichloromethane
  7. filtrationThe solid is filtered
  8. customdried

Sources & evidence

ORD record
ord-2e7dc30aab094001946aa06b797b6275
Source dataset
uspto-grants-2013_08
Patent number
US08513307B2

Reaction notes

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