HCID 13476527, compound → HCID 13476528, compound

HRID 1156335Notes

Reaction equation

HRID 1156335 reaction equation
[C:1]([N:9]1[CH:14]=[CH:13][CH:12]([C:15]2[C:23]3[C:18](=[CH:19][C:20]([F:24])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH:11]=[CH:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].CN(C)C(=O)C>[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[C:23]3[C:18](=[CH:19][C:20]([F:24])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 13476527HCID 13476527, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13476528HCID 13476528, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 95 parts of 1-benzoyl-4-(6-fluoro-1H-indol-3-yl)-1,4-dihydropyridine and 540 parts of N,N-dimethylacetamide is hydrogenated in the Parr-apparatus with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off over Hyflo and the filtrate is poured onto water while stirring: an oil is precipitated. The supernatant aqueous phase is decanted and the residual oil is washed with water. The oily product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is washed successively with a mixture of petroleumether and 2,2'-oxybispropane, with a hydrochloric acid solution 2 N and with water, and dissolved in trichloromethane. The latter is washed with a sodium hydroxide solution 1 N and with water, dried, filtered and evaporated. The residue is heated in a small amount of N,N-dimethylacetamide at 80° C. and the mixture is allowed to stand over week-end. The solid product is filtered off, washed with a mixture of water and ethanol, and dried in vacuo at 80° C., yielding 25 parts of 1-benzoyl-4-(6-fluoro-1H-indol-3-yl)-piperidine; mp. 220° C.

Workup

  1. filtrationthe catalyst is filtered off over Hyflo
  2. additionthe filtrate is poured onto water
  3. customan oil is precipitated
  4. customThe supernatant aqueous phase is decanted
  5. washthe residual oil is washed with water
  6. extractionThe oily product is extracted with trichloromethane
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated
  10. washThe residue is washed successively with a mixture of petroleumether and 2,2'-oxybispropane, with a hydrochloric acid solution 2 N and with water
  11. dissolutiondissolved in trichloromethane
  12. washThe latter is washed with a sodium hydroxide solution 1 N and with water
  13. customdried
  14. filtrationfiltered
  15. customevaporated
  16. waitto stand over week-end
  17. filtrationThe solid product is filtered off
  18. washwashed with a mixture of water and ethanol
  19. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-4e645a106983425387eacbb2144508e9
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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