Sodium Hydroxide → 1-Methyl-4-(1,2,5,6-tetrahydro-3-pyridinyl)-1H-indole

HRID 1155685Notes

Reaction equation

HRID 1155685 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[C:6](=[C:7]([C:12]3(O)[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[OH-].[Na+]>Cl>[CH3:2][N:3]1[C:11]2[C:6](=[C:7]([C:12]3[CH2:13][NH:14][CH2:15][CH2:16][CH:17]=3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20537466HCID 20537466, compound

Product 1

HCID 205374961-Methyl-4-(1,2,5,6-tetrahydro-3-pyridinyl)-1H-indoleYield 62.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 12 g of the product of Example 19 in 360 ml of 1 N hydrochloric acid was refluxed for 4 hours and was cooled in an ice bath while adding sodium hydroxide solution until the pH was alkaline. The mixture was extracted with methylene chloride and the organic phase was washed with aqueous sodium chloride solution, dried over magnesium sulfate and distilled to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 6-3-1 chloroform-acetone-triethylamine mixture to obtain 6 g of 1-methyl-4-(1,2,5,6-tetrahydropyridin-3-yl)-1H-indole.

Workup

  1. temperaturewas cooled in an ice bath
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe organic phase was washed with aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with a 6-3-1 chloroform-acetone-triethylamine mixture

Sources & evidence

ORD record
ord-38be4f7ca8bc4b89b048ff51e351d93b
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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