1-Cyano-1-(4-diethylaminophenyl)cyclopentane → [1-(4-Diethylaminophenyl)cyclopentyl]methylamine

HRID 2050900Notes

Reaction equation

HRID 2050900 reaction equation
[C:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[H][H]>[Ni].N>[CH2:17]([N:14]([CH2:15][CH3:16])[C:11]1[CH:12]=[CH:13][C:8]([C:3]2([CH2:1][NH2:2])[CH2:4][CH2:5][CH2:6][CH2:7]2)=[CH:9][CH:10]=1)[CH3:18]

Participants

5

Reactant 2

HCID 198341171-Cyano-1-(4-diethylaminophenyl)cyclopentaneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19834131[1-(4-Diethylaminophenyl)cyclopentyl]methylamineYield 93.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

In a pressure reactor was placed 10.4 g (0.043 mole) of 1-cyano-1-(4-diethylaminophenyl)cyclopentane, 100 mL of methanolic ammonia, and 10 g of Ra-Ni catalyst. The reactor was charged with hydrogen and shaken at room temperature until the theoretical amount of hydrogen was taken up. The reaction mixture was filtered and the filtrate concentrated in vacuo to yield 9.9 g of the desired amine.

Workup

  1. customIn a pressure reactor was placed
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-c1d4e710b5c9479f910185445f53c873
Source dataset
uspto-grants-1991_05
Patent number
US05015644

Reaction notes

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