9-Benzyl-9-azabicyclo[3.3.1]nonan-3-one--hydrogen chloride (1/1) → 9-Azabicyclo[3.3.1]nonan-3-one--hydrogen chloride (1/1)

HRID 1393228Notes

Reaction equation

HRID 1393228 reaction equation
[ClH:1].C([N:9]1[CH:14]2[CH2:15][CH2:16][CH2:17][CH:10]1[CH2:11][C:12](=[O:18])[CH2:13]2)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[ClH:1].[CH:10]12[NH:9][CH:14]([CH2:15][CH2:16][CH2:17]1)[CH2:13][C:12](=[O:18])[CH2:11]2

Participants

4

Reactant 1

HCID 241908609-Benzyl-9-azabicyclo[3.3.1]nonan-3-one--hydrogen chloride (1/1)

Product 1

HCID 197915239-Azabicyclo[3.3.1]nonan-3-one--hydrogen chloride (1/1)Yield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

9-benzyl-9-azabicyclo[3.3.1]nonan-3-one hydrochloride (38.8 g) was dissolved in 450 mL of glacial acetic acid. 13.5 Grams of 10% Pd/C (Degussa catalyst E101—containing 50% water) was added. After the appropriate evacuation & purge cycles, the mixture was agitated under 62 psi of H2 at rt overnight. TLC (3% MeOH in CH2Cl2 on silica gel) indicated that the reaction was complete. The reaction mixture was filtered through Celite and concentrated by rotary evaporation under vacuum. The product was redissolved in 0.12 N HCl (250 mL) and the solution was concentrated in vacuo. This was repeated once more with 0.12 N HCl (250 mL). The product was then dissolved in 1 N HCl and concentrated to dryness under vacuum. A sticky brown solid was obtained. The material was recrystallized once from isopropanol and once from EtOH to give 9-azabicyclo[3.3.1]nonan-3-one hydrochloride as a tan granular solid (18.8 g; 73.6% yield) after drying under high vacuum (0.1-1.0 mTorr) overnight.

Workup

  1. customAfter the appropriate evacuation & purge cycles
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated by rotary evaporation under vacuum
  4. dissolutionThe product was redissolved in 0.12 N HCl (250 mL)
  5. concentrationthe solution was concentrated in vacuo
  6. dissolutionThe product was then dissolved in 1 N HCl
  7. concentrationconcentrated to dryness under vacuum
  8. customA sticky brown solid was obtained
  9. customThe material was recrystallized once from isopropanol and once from EtOH

Sources & evidence

ORD record
ord-1f0212d1a98849f89aae1ab93e32c204
Source dataset
uspto-grants-2008_03
Patent number
US07345056B2

Reaction notes

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