2-Azaspiro[5.5]undec-1-ene → 2-Azaspiro[5.5]undecane

HRID 2164727Notes

Reaction equation

HRID 2164727 reaction equation
[CH:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][N:2]=1.[H][H]>[Ni].C(O)C>[CH2:1]1[C:6]2([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:5][CH2:4][CH2:3][NH:2]1

Participants

5

Reactant 2

HCID 18835922-Azaspiro[5.5]undec-1-eneHCID 178418361HCID 178418361, compound

Product 1

HCID 50061172-Azaspiro[5.5]undecaneYield 88.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-azaspiro-[5.5]-undec-1-ene (15 g.; 0.10 mole) and one teaspoon (3 g.) of W2 Raney nickel catalyst in absolute ethanol (300 ml.) is hydrogenated at an initial pressure of B 40 psi until hydrogen uptake ceases (2 hours). The mixture is filtered through celite and the filtrate concentrated under reduced pressure. Distillation of the residual liquid yields 88% of 2-azaspiro-[5.5]-undecane (13.5 g.), b.p. 55°-57° C./0.10 mm.

Workup

  1. filtrationThe mixture is filtered through celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. distillationDistillation of the residual liquid

Sources & evidence

ORD record
ord-33e67b5e3a984a11be32cc748201282a
Source dataset
uspto-grants-1985_03
Patent number
US04507291

Reaction notes

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