Sodium Hydroxide → HCID 20537481, compound

HRID 1155688Notes

Reaction equation

HRID 1155688 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C:4]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[CH3:18])(O)[CH2:3]1.[OH-].[Na+]>Cl>[CH3:18][N:13]1[C:14]2[C:10](=[C:9]([C:4]3[CH2:3][N:2]([CH3:1])[CH2:7][CH2:6][CH:5]=3)[CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20537468HCID 20537468, compound

Product 1

HCID 20537481HCID 20537481, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 15 g of 1-methyl-3-(1-methyl-1H-indol-4-yl)-3-piperidinol in 500 ml of 1 N hydrochloric acid was refluxed for 3 hours and was then cooled to room temperature and stirred for 16 hours. The mixture was cooled in an ice bath while adding sodium hydroxide until the mixture was alkaline and the mixture was extracted with ethyl acetate. The organic phase was washed with aqueous sodium chloride solution, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The 13 g of residue was chromatographed over silica gel and eluted with a 6-3-1 cyclohexanechloroform-triethylamine mixture to obtain 8.7 g of 1-methyl-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe 13 g of residue was chromatographed over silica gel
  7. washeluted with a 6-3-1 cyclohexanechloroform-triethylamine mixture

Sources & evidence

ORD record
ord-3bdaa1eee9f04bf8a1d2845f97b6497b
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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