HCID 19390880, compound → HCID 19390920, compound

HRID 1645870Notes

Reaction equation

HRID 1645870 reaction equation
[ClH:1].Cl.C([N:10]1[CH2:15][CH:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)C1C=CC=CC=1>C(O)C.O.[Pd]>[ClH:1].[ClH:1].[CH3:23][N:22]([CH3:24])[C:19]1[CH:18]=[CH:17][C:16]([CH:13]2[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]2)=[CH:21][CH:20]=1

Participants

5

Reactant 1

HCID 19390880HCID 19390880, compound

Product 1

HCID 19390920HCID 19390920, compoundYield 86.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-Benzyl-4-(4-dimethylaminophenyl)-1,2,3,6-tetrahydropyridine dihydrochloride (3.65 g) prepared in Example 46 was dissolved in a solvent mixture of 20 ml of ethanol and 5 ml of water. Using 10% palladium-on-carbon as the catalyst, the mixture was subjected to catalytic reduction at atmospheric temperature and pressure for 10 hours. The catalyst was then filtered off and the solvent was distilled off. The residual oil was diluted with a saturated aqueous solution of sodium chloride, made basic by addition of solid sodium hydrogen carbonate and extracted with acetonitrile. The extract was dried and 5 ml of 2N-ethanolic hydrochloric acid was added. Finally the solvent was distilled off and the residue was recrystallized from ethanol to give 1.2 g of colorless crystals melting at 215°-220° C.

Workup

  1. filtrationThe catalyst was then filtered off
  2. distillationthe solvent was distilled off
  3. additionThe residual oil was diluted with a saturated aqueous solution of sodium chloride
  4. additionmade basic by addition of solid sodium hydrogen carbonate
  5. extractionextracted with acetonitrile
  6. customThe extract was dried
  7. addition5 ml of 2N-ethanolic hydrochloric acid was added
  8. distillationFinally the solvent was distilled off
  9. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-3d8e98f037524343ae9be8d754c4ad61
Source dataset
uspto-grants-1993_01
Patent number
US05177087

Reaction notes

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