Cyclopentanone → 2-amino-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile

HRID 1916263Notes

Reaction equation

HRID 1916263 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:7](=[C:14]([C:17]#[N:18])[C:15]#[N:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])(=O)C.[NH4+:23]>C1(C)C=CC=CC=1>[NH2:18][C:17]1[N:23]=[C:2]2[CH2:3][CH2:4][CH2:5][C:1]2=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 17608Malononitrile, benzylidene-HCID 517165Ammonium Acetate

Product 1

HCID 6681092-amino-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 12 ml of toluene, 500 mg (5.94 mmol) of cyclopentanone, 916 mg (5.94 mmol) of benzylidenemalononitrile and 1.00 g (13.1 mmol) of ammonium acetate were heated under reflux for 2 h. The mixture was washed with 10 ml of a saturated aqueous sodium bicarbonate solution and then with 10 ml of water, dried over magnesium sulfate and freed from the solvent on a rotary evaporator. The residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. temperatureunder reflux for 2 h
  2. washThe mixture was washed with 10 ml of a saturated aqueous sodium bicarbonate solution
  3. dry with materialwith 10 ml of water, dried over magnesium sulfate
  4. customfreed from the solvent on a rotary evaporator
  5. customThe residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-41e05908442b48b183375f9c5b21ceeb
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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