Water → HCID 14088189, compound

HRID 2408341Notes

Reaction equation

HRID 2408341 reaction equation
[CH2:1]([NH:8][C:9]1([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[K+]>CCOCC>[NH2:15][CH2:14][C:9]1([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21581542HCID 21581542, compound

Product 1

HCID 14088189HCID 14088189, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

14.1 g of 1-(benzylamino)cyclopentanecarbonitrile are solubilized in 300 mL of Et2O. The mixture is cooled and then 10.68 g of LiAlH4 are added in fractions, while maintaining the temperature in T° C. to −5° C.-0° C. Stirring is applied and under nitrogen at 0° C. for 1 h. After return to RT, 11 mL H2O and then 11 mL of 15% KOH and finally 33 mL of H2O are added dropwise while maintaining the temperature less than 15° C. The precipitate is filtered on Celite, and then the organic phase is dried on magnesium sulfate. The solvents are dry evaporated. 14.23 g (yield=99%) of 1-(aminomethyl)-N-benzylcyclopentanamine are obtained as a yellowish oil.

Workup

  1. temperatureThe mixture is cooled
  2. temperaturewhile maintaining the temperature in T° C
  3. customto −5° C.-0° C
  4. temperaturewhile maintaining the temperature less than 15° C
  5. filtrationThe precipitate is filtered on Celite
  6. customthe organic phase is dried on magnesium sulfate
  7. customThe solvents are dry
  8. customevaporated

Sources & evidence

ORD record
ord-4a5602e425c44370856106243fe86188
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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