HCID 13210550, compound → HCID 13210552, compound

HRID 1903173Notes

Reaction equation

HRID 1903173 reaction equation
[CH:1]([C@@H:3]1[C@H:8]([CH2:9][CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:7][CH2:6][NH:5][CH2:4]1)=[CH2:2]>Cl.CO.[Pt]=O>[CH2:1]([C@@H:3]1[C@H:8]([CH2:9][CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:7][CH2:6][NH:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 1

HCID 13210550HCID 13210550, compound

Product 1

HCID 13210552HCID 13210552, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

0.250 g of 3-{[3-(R)vinyl-4(R)piperidyl]-ethyl}-indole in 1 ml of normal hydrochloric acid and 9 ml of methanol in the presence of 0.04 g of platinum oxide as catalyst were hydrogenated for 3 hours at ambient temperature and at atmospheric pressure. The catalyst was filtered, the filtrate evaporated to dryness, the residue made up in 100 ml of water, the aqueous phase washed with ether and alkalinized with an aqueous solution of sodium hydroxide and the insoluble substance was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and evaporated to dryness under reduced pressure. 0.180 g of product which melted at 150° C. was obtained.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated to dryness
  3. washthe aqueous phase washed with ether
  4. extractionthe insoluble substance was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6a40371fe7174081a8792f973e8e90f3
Source dataset
uspto-grants-1984_03
Patent number
US04435410

Reaction notes

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