HCID 23313762, compound → HCID 23313727, compound

HRID 745550Notes

Reaction equation

HRID 745550 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH:14]2[C:19](=[O:20])[CH:18]3[CH2:21][CH2:22][N:15]2[CH2:16][CH2:17]3)=[CH:7][CH:6]=1)([O-])=O>[Pd].CO>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH2:13][CH:14]2[C:19](=[O:20])[CH:18]3[CH2:21][CH2:22][N:15]2[CH2:16][CH2:17]3)=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 23313762HCID 23313762, compound

Product 1

HCID 23313727HCID 23313727, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a Parr bottle add 9.74 g (0.03 mole) of 2-[3-(4-nitrophenyl)propyl]-1-azabicyclo[2.2.2]octan-3-one hydrochloride, 150 ml of methanol and 0.5 g of 10% palladium on charcoal catalyst (wet with 2-3 ml of water). Place the bottle on a hydrogenator, flush the system three times with hydrogen and pressurize the system to 25 p.s.i. Shake the reaction mixture and follow the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 95:5). At the completion of the reaction remove the catalyst by vacuum filtration. Wash the catalyst with methanol, to the filtrate add 5 ml of concentrated hydrochloric acid. Remove the solvent in vacuo to afford the title compound.

Workup

  1. customflush the system three times with hydrogen
  2. customthe reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 95:5)
  3. customAt the completion of the reaction remove the catalyst
  4. filtrationby vacuum filtration
  5. washWash the catalyst with methanol
  6. additionto the filtrate add 5 ml of concentrated hydrochloric acid
  7. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-e94cfa19271245fb8b695aebed43f22f
Source dataset
uspto-grants-1986_07
Patent number
US04599344

Reaction notes

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