Ammonia → 4-Cyclohexylquinuclidine

HRID 1533027Notes

Reaction equation

HRID 1533027 reaction equation
[C:1]1([C:7]23[CH2:14][CH2:13][N:10]([CH2:11][CH2:12]2)[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N>C(O)(=O)C.O.[Rh]>[CH:1]1([C:7]23[CH2:14][CH2:13][N:10]([CH2:9][CH2:8]2)[CH2:11][CH2:12]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 1428104-Phenyl-1-azabicyclo(2.2.2)octane

Product 1

HCID 226138404-CyclohexylquinuclidineYield 91.1%

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-Phenylquinuclidine (5 g) (see J. Org. Chem., 22, 1484, (1957)) was dissolved in glacial acetic acid (25 ml), 5% w/w rhodium-on-alumina (2 g) was added and the mixture hydrogenated for 5 days at 345 kPa (50 psi). The mixture was filtered through a short column of Arbacel (trade mark) filter aid and the pad washed with methanol. The filtrate was collected and the solvent removed under reduced pressure to give a residue which was dissolved in water. The pH was adjusted to >10 by addition of 0.88 aqueous ammonia solution. The aqueous mixture was extracted with ethyl acetate (×3) and the organic layers combined, washed with brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give 4-cyclohexylquinuclidine (4.7 g) as a pale pink solid.

Workup

  1. filtrationThe mixture was filtered through a short column of Arbacel (trade mark)
  2. filtrationfilter aid
  3. washthe pad washed with methanol
  4. customThe filtrate was collected
  5. customthe solvent removed under reduced pressure
  6. customto give a residue which
  7. extractionThe aqueous mixture was extracted with ethyl acetate (×3)
  8. washwashed with brine
  9. dry with materialdried over anhydrous sodium sulphate
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-270de4f43dc74d97a579ddcace21cc6e
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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