1-Phenylcyclopentanecarbonitrile → (1-Phenylcyclopentyl)methanamine

HRID 1497672

Reaction equation

HRID 1497672 reaction equation
[C:1]1([C:7]2([C:12]#[N:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([C:7]2([CH2:12][NH2:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 661681-PhenylcyclopentanecarbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 205131(1-Phenylcyclopentyl)methanamineYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-phenyl-cyclopentanecarbonitrile (4 g, 23.5 mmol) in tetrahydrofuran (50 mL) was added lithium aluminium hydride slowly (1M in tetrahydrofuran, 70 ml, 70.6 mmol) and the reaction mixture was stirred at room temperature for 2 h. After completion of the reaction, the reaction mixture was quenched with saturated aqueous Na2SO4 solution slowly at 0° C. It was then filtered and the residue was washed with ethyl acetate. The organic part was concentrated to get C-(1-phenyl-cyclopentyl)-methylamine (8) (2.5 g, crude) as a liquid.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was quenched with saturated aqueous Na2SO4 solution slowly at 0° C
  3. filtrationIt was then filtered
  4. washthe residue was washed with ethyl acetate
  5. concentrationThe organic part was concentrated

Sources & evidence

ORD record
ord-382086c9ccc94cde99b05d0f0dc1da0c
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Linked notes

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