HCID 67789338, compound → (3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride

HRID 1742819Notes

Reaction equation

HRID 1742819 reaction equation
[ClH:1].[NH2:2][CH:3]1[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[C@@H:4]1NC(=O)C1C=CC=C([Cl:19])C=1>Cl>[ClH:19].[ClH:1].[NH2:2][C@H:3]1[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1

Participants

3

Reactant 1

HCID 67789338HCID 67789338, compound

Product 1

HCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochlorideYield 97.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 11.2 g of (S)-(-)-N-(3-aminoquinuclidinyl)-3-chlorobenzamide hydrochloride was added 40 ml of concentrated hydrochloric acid and the mixture was refluxed for 6 hours. The reaction mixture was cooled and filtered to remove insolubles and the filtrate was concentrated and dried. To the residue was added ethanol and the resulting crystals were recovered by filtration to provide 6.9 g of (S)-(-)-3-aminoquinuclidine dihydrochloride. m.p. not lower than 260° C.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customto remove insolubles
  5. concentrationthe filtrate was concentrated
  6. customdried
  7. additionTo the residue was added ethanol
  8. filtrationthe resulting crystals were recovered by filtration

Sources & evidence

ORD record
ord-e9837aff524147caacc4a93ef8a08679
Source dataset
uspto-grants-1994_08
Patent number
US05342845

Reaction notes

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