Sodium Hydroxide → HCID 20537489, compound

HRID 1155687Notes

Reaction equation

HRID 1155687 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][N:15]3[CH3:20])(O)[CH2:5]1)[CH2:2][CH3:3].[OH-].[Na+]>Cl>[CH3:20][N:15]1[C:16]2[C:12](=[C:11]([C:6]3[CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8][CH:7]=3)[CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20537493HCID 20537493, compound

Product 1

HCID 20537489HCID 20537489, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 8.2 g of 1-propyl-3-(1-methyl-1H-indol-4-yl)-3-piperidinol in 250 ml of 1 N hydrochloric acid was refluxed for 4 hours and while cooling in an ice bath, sodium hydroxide solution was added thereto until the pH was alkaline. The mixture was extracted with methylene chloride and the organic phase was washed with aqueous sodium chloride solution, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 9-1 cyclohexane-triethylamine mixture to obtain 6.2 g of 1-methyl-4-(1-propyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole with an Rf=0.2.

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe organic phase was washed with aqueous sodium chloride solution
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with a 9-1 cyclohexane-triethylamine mixture

Sources & evidence

ORD record
ord-4ffb75d5cf184ca4b88d09961ab39b04
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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