Cyclopentanone → HCID 57672608, compound

HRID 1192857Notes

Reaction equation

HRID 1192857 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.[C:13]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14]1.[Si]([C:23]#[N:24])(C)(C)C>C(OCC)(=O)C>[C:23]([C:13]1([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]#[N:12])=[CH:6][CH:7]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1)#[N:24]

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 82115Trimethylsilyl cyanideHCID 12547487HCID 12547487, compound

Product 1

HCID 57672608HCID 57672608, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(4-Aminophenyl)butanenitrile (97) (52 mg, 0.27 mmol), cyclopentanone (0.07 mL, 0.55 mmol) and TMSCN (0.05 mL, 0.55 mmol) was heated to 80° C. and stirred for 13 h. To the medium was added ethyl acetate (2×20 mL) and then washed with water (2×20 mL). The organic layer was dried over MgSO4, concentrated and the residue was purified with silica gel column chromatography (hexane:ethyl acetate, 1:1) to give 4-[4-(1-Cyanocyclopentyl amino)phenyl]butanenitrile (93) (70 mg, quant.) as a white solid.

Workup

  1. washwashed with water (2×20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-00751c64cc8447f69d6bafea79bd9853
Source dataset
uspto-grants-2014_03
Patent number
US08680291B2

Reaction notes

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