Potassium Carbonate → HCID 3068359, compound

HRID 1155691Notes

Reaction equation

HRID 1155691 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][C:6]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)(O)[CH2:5]1)[CH:2]=[CH2:3].[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>Cl>[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]=[C:6]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 20537467HCID 20537467, compound

Product 1

HCID 3068359HCID 3068359, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 14 g of the product of Example 27 in 400 ml of hydrochloric acid was refluxed for 4 hours and the mixture was iced and made alkaline with sodium hydroxide. Potassium carbonate was added to the mixture which was then extracted with ethyl acetate. The organic phase was dried and evaporated to dryness under reduced pressure and the 12.7 g of residue were chromatographed over silica gel. Elution with a 9-1 chloroform-acetone mixture yielded 6.85 g of 4-[1-(2-propenyl)-1,2,5,6-tetrahydropyridin-3-yl]-1H-indole with an Rf=0.15.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. customThe organic phase was dried
  3. customevaporated to dryness under reduced pressure
  4. customthe 12.7 g of residue were chromatographed over silica gel
  5. washElution with a 9-1 chloroform-acetone mixture

Sources & evidence

ORD record
ord-5d27f942fd284967bc86634873cf0df3
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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