Cyclopentanone → 1-((4-Bromo-3,5-dimethylphenyl)amino)cyclopentanecarbonitrile

HRID 1487098Notes

Reaction equation

HRID 1487098 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:7][C:8]1[C:14]([CH3:15])=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[CH3:16].C[Si]([C:21]#[N:22])(C)C>C(O)(=O)C>[Br:7][C:8]1[C:14]([CH3:15])=[CH:13][C:11]([NH:12][C:1]2([C:21]#[N:22])[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][C:9]=1[CH3:16]

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 82115Trimethylsilyl cyanideHCID 123831174-Bromo-3,5-dimethylaniline

Product 1

HCID 902248911-((4-Bromo-3,5-dimethylphenyl)amino)cyclopentanecarbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of cyclopentanone (42 mg, 0.500 mmol) and 4-bromo-3,5-dimethylaniline (100 mg, 0.500 mmol) in acetic acid (0.5 mL), trimethylsilyl cyanide (0.063 ml, 0.500 mmol) was added at room temperature. The mixture was stirred at room temperature for 1.5 hours under nitrogen atmosphere. The reaction mixture was quenched with 28% aqueous ammonia (1 mL), diluted with water and extracted with dichloromethane. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to afford 1-((4-bromo-3,5-dimethylphenyl)amino)cyclopentanecarbonitrile as a crude product (152 mg).

Workup

  1. additionwas added at room temperature
  2. customThe reaction mixture was quenched with 28% aqueous ammonia (1 mL)
  3. additiondiluted with water
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a25f0f70319428e975caa0bd8e9ff21
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

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