Hydrochloric Acid → 5-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indole

HRID 1277644Notes

Reaction equation

HRID 1277644 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2.[OH-].[NH4+]>C(O)(=O)C>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[C:6]1[CH2:5][CH2:4][NH:3][CH2:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 138725-MethoxyindoleHCID 14923Ammonium HydroxideHCID 21584170Piperidin-4-one hydrate

Product 1

HCID 1080295-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

44 g of the hydrochloride of 4-piperidone monohydrate were added at 100° C. to a solution of 12.6 g of 5-methoxy-indole in 240 ml of acetic acid and the mixture was held at 100° C. for 30 minutes and was then cooled and poured into ice water containing 400 ml of concentrated ammonium hydroxide solution. The mixture was extracted with ethyl acetate and the organic phase was washed with aqueous sodium chloride solution, was dried over magnesium sulfate and was evaporated to dryness to obtain 20 g of raw product. The latter was chromatographed over silica gel and elution with a 7-2-1 chloroform-methanol-triethylamine mixture yielded 5.26 g of 5-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in the form of a resin.

Workup

  1. temperaturewas then cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with aqueous sodium chloride solution
  4. dry with materialwas dried over magnesium sulfate
  5. customwas evaporated to dryness
  6. customto obtain 20 g of raw product
  7. customThe latter was chromatographed over silica gel and elution with a 7-2-1 chloroform-methanol-triethylamine mixture

Sources & evidence

ORD record
ord-ed06624d72f14758b6e4364b0043425c
Source dataset
uspto-grants-1981_07
Patent number
US04278677

Reaction notes

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