Water → 8-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride

HRID 268218Notes

Reaction equation

HRID 268218 reaction equation
O.[ClH:2].Cl.C([N:11]1[CH2:17][CH:16]2[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]2)[CH2:12]1)C1C=CC=CC=1.O>C(O)C.[Pd]>[ClH:2].[ClH:2].[CH3:19][N:18]1[CH:13]2[CH2:14][CH2:15][CH:16]1[CH2:17][NH:11][CH2:12]2

Participants

5

Reactant 2

HCID 962WaterHCID 215454913-Benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride monohydrate

Product 1

HCID 221201898-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochlorideYield 152.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride monohydrate (18.1 g, 0.059 mole) in absolute ethanol (200 ml) and 10% palladium on charcoal (3.0 g) was hydrogenated for 2 hours at atmospheric pressure. Sufficient water was added to dissolve the insoluble hydrochloride salt that had formed, and the reaction was filtered. The filtrate was evaporated in vacuo, the residue was triturated in hot absolute ethanol, and the mixture was filtered to yield 8.98 g of 8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride, melting point 315°C (dec.). The mother liquor was treated with ethanolic dry hydrogen chloride to afford an additional 2.28 g. Yield: 12.26 g (96%).

Workup

  1. customhad formed
  2. filtrationthe reaction was filtered
  3. customThe filtrate was evaporated in vacuo
  4. customthe residue was triturated in hot absolute ethanol
  5. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-e60ddb19b937414ebb6aed244c29f12b
Source dataset
uspto-grants-1976_03
Patent number
US03947445

Reaction notes

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