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

HRID 1995637Notes

Reaction equation

HRID 1995637 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 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-40f1904dd9f9455ab5f8769b906c3944
Source dataset
uspto-grants-1983_09
Patent number
US04405630

Reaction notes

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