Acetic Acid → HCID 23453023, compound

HRID 1277654Notes

Reaction equation

HRID 1277654 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[C:6]([O:11][CH3:12])[CH:5]=2.[ClH:13].O.[NH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.C(O)(=O)C>C(O)(C)C>[ClH:13].[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH:17]=1)=[CH:8][CH:7]=[C:6]([O:11][CH3:12])[CH:5]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 108447096-methoxy-2-methyl-1H-indoleHCID 21584170Piperidin-4-one hydrate

Product 1

HCID 23453023HCID 23453023, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 2 g of 2-methyl-6-methoxy-1H-indole, 4 g of the hydrochloride of 4-piperidone monohydrate and 40 ml of acetic acid was stirred at 100° C. under an inert atmosphere for 90 minutes and the mixture was cooled and poured into a solution of 150 g of ice and 80 ml of 22° Be ammonium hydroxide. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried over magnesium sulfate and evaporated to dryness and reduced pressure. The residue was empasted with hot ethyl acetate and the mixture was cooled and vacuum filtered. The product was washed with ethyl acetate and dried under reduced pressure to obtain 2.5 g of raw product which was dissolved in 50 ml of hot isopropanol. The solution was cooled and made acidic by dropwise addition of an isopropanol solution of gaseous hydrogen chloride. The mixture stood overnight after crystallization was induced and was vacuum filtered. The product was washed with isopropanol and was dried under reduced pressure to obtain 2.25 of 2-methyl-6-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride melting at 270° C.

Workup

  1. temperaturethe mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness and reduced pressure
  6. temperaturethe mixture was cooled
  7. filtrationvacuum filtered
  8. washThe product was washed with ethyl acetate
  9. customdried under reduced pressure
  10. customto obtain 2.5 g of raw product which
  11. temperatureThe solution was cooled
  12. waitThe mixture stood overnight
  13. customafter crystallization
  14. filtrationfiltered
  15. washThe product was washed with isopropanol
  16. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-89bec86c18634e0e98e8e51f894986f3
Source dataset
uspto-grants-1981_07
Patent number
US04278677

Reaction notes

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