Aniline → 1-(phenylamino)cyclopentanecarbonitrile

HRID 1666722Notes

Reaction equation

HRID 1666722 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=O)[CH2:12][CH2:11][CH2:10][CH2:9]1.C[Si]([C:18]#[N:19])(C)C>C(O)(=O)C>[C:2]1([NH:1][C:8]2([C:18]#[N:19])[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 8452Cyclopentanone2×HCID 82115Trimethylsilyl cyanide

Product 1

HCID 2430951-(phenylamino)cyclopentanecarbonitrileYield 91.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.9 ml (31.8 mmol) of aniline (starting product 2) are added to a solution of 2.6 ml (29.4 mmol) of cyclopentanone (starting product 3) in 30 ml of acetic acid at 0° C. The solution is stirred for 15 minutes and 4 ml (30 mmol) of trimethylsilyl cyanide are added. The reaction medium is stirred for one night at room temperature and then gently poured into an ice-cold ammonium hydroxide solution while keeping the pH basic and extracted with dichloromethane. The organic phases are collected and washed with water. They are dried over sodium sulfate. The solvents are evaporated and then the residue is chromatographed on silica gel (heptane/ethyl acetate 90/10, v/v). 5 g of 1-phenylaminocyclopentanecarbonitrile are obtained in the form of a clear brown oil. Yield=91%.

Workup

  1. stirringThe reaction medium is stirred for one night at room temperature
  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 solvents are evaporated
  7. customthe residue is chromatographed on silica gel (heptane/ethyl acetate 90/10

Sources & evidence

ORD record
ord-4230310b57dd42d9bc8375e311f011df
Source dataset
uspto-grants-2011_10
Patent number
US08044082B2

Reaction notes

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