Cyclopentanone → HCID 68631576, compound

HRID 1945176Notes

Reaction equation

HRID 1945176 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10]1.C[Si]([C:19]#[N:20])(C)C.[OH-].[NH4+]>C(O)(=O)C>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:9]2([C:19]#[N:20])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 108934-IodoanilineHCID 14923Ammonium HydroxideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 68631576HCID 68631576, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.5 g (16 mmol) of 4-iodo-aniline are added to a solution of 1.3 ml (14.7 mmol) of cyclopentanone in 20 ml of acetic acid at 0° C. The solution is stirred for 15 minutes and 2 ml (15 mmol) of trimethylsilyl cyanide are added. The reaction medium is stirred for one night at ambient temperature. It is then poured gently into a solution of ice-cooled ammonium hydroxide until the pH is basic and extracted with dichloromethane. The organic phases are combined and washed with water. They are dried over sodium sulfate. After evaporation of the solvents, 4.3 g of 1-(4-iodo-phenylamino)-cyclopentanecarbonitrile are obtained in the form of a brown oil. (Yield=94%).

Workup

  1. stirringThe reaction medium is stirred for one night at ambient temperature
  2. additionIt is then poured gently into a solution of ice-
  3. extractionextracted with dichloromethane
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customAfter evaporation of the solvents, 4.3 g of 1-(4-iodo-phenylamino)-cyclopentanecarbonitrile
  7. customare obtained in the form of a brown oil

Sources & evidence

ORD record
ord-41d4b722a1fe4aa782e7286064983622
Source dataset
uspto-grants-2013_03
Patent number
US08394990B2

Reaction notes

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