1-Benzylcyclopentane-1-carbonitrile → HCID 18999642, compound

HRID 274118Notes

Reaction equation

HRID 274118 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([CH2:13][C:14]2([C:19]#[N:20])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[C:7]1([CH2:13][C:14]2([CH2:19][NH2:20])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 124025631-Benzylcyclopentane-1-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 18999642HCID 18999642, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 68.8 g (1.81 mole) of LiAlH4 in 1350 ml anhydrous ether, under an atmosphere of nitrogen, there are poured dropwise during 1.5 hour, while keeping the temperature of the reaction mixture between 10° and 20° C., 279.9 g (1.51 mole) of 1-[(phenyl)methyl]cyclopentanecarbonitrile (prepared according to Campaigne E. and Forsh R. A., J. Org. Chem. (1978) 43, 1044-50). After stirring at room temperature during 18 hours, the excess of hydride is destroyed by adding 344 ml water. The organic phase is dried over Na2SO4 and filtered. The filtrate which is concentrated under reduced pressure is distilled to give 273.9 g (yield=95.8%) of a colorless liquid. b.p.2 =122° C.

Workup

  1. additionunder an atmosphere of nitrogen, there are poured dropwise during 1.5 hour
  2. customprepared
  3. customthe excess of hydride is destroyed
  4. additionby adding 344 ml water
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate which is concentrated under reduced pressure
  8. distillationis distilled

Sources & evidence

ORD record
ord-724e54fb37b1465f8480bbba166a4814
Source dataset
uspto-grants-1995_02
Patent number
US05387709

Reaction notes

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