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

HRID 2049024Notes

Reaction equation

HRID 2049024 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-1H-indole in 240 ml of acetic acid and the mixture was held at 100° C. for 30 minutes and was then cooled. The mixture was poured into ice water containing 400 ml of concentrated ammonium hydroxide and was extracted with ethyl acetate. The organic phase was washed with aqueous sodium chloride solution, dried over magnesium sulfate and evaporated to dryness to obtain 20 g of raw product. The latter was chromatographed over silica gel and was eluted with a 7-2-1 chloroform-methanol-triethylamine mixture to obtain 5.26 g of 5-methoxy-3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indole in the form of a resin.

Workup

  1. temperaturewas then cooled
  2. extractionwas 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
  6. customto obtain 20 g of raw product
  7. customThe latter was chromatographed over silica gel
  8. washwas eluted with a 7-2-1 chloroform-methanol-triethylamine mixture

Sources & evidence

ORD record
ord-a1da44aa4352424cb6ad12af3bf1d805
Source dataset
uspto-grants-1980_04
Patent number
US04196209

Reaction notes

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