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

HRID 2198471Notes

Reaction equation

HRID 2198471 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-f1f66288348d485fa8ccea001bbe3609
Source dataset
uspto-grants-1982_11
Patent number
US04357471

Reaction notes

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