Acetic Acid → HCID 19866449, compound

HRID 1199352Notes

Reaction equation

HRID 1199352 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[CH3:9][O:10][C:11]1[C:12](OC)=[C:13]([O:17][CH3:18])[CH:14]=[CH:15][CH:16]=1.[C:21](O)(=[O:23])C>>[CH3:1][N:2]1[CH2:7][CH:6]=[CH:5][CH:4]([C:12]2[C:13]([O:17][CH3:18])=[CH:14][C:15]([O:23][CH3:21])=[CH:16][C:11]=2[O:10][CH3:9])[CH2:3]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 124621,2,3-TrimethoxybenzeneHCID 13603N-Methyl-2-piperidone

Product 1

HCID 19866449HCID 19866449, compound

Procedure

N-methylpiperidone (2.8 mol) is added with stirring to a solution of trimethoxybenzene (2.38 mol) in glacial acetic acid (750 ml), the temperature of the reaction mixture being maintained below 25° C. After the addition has ended, hydrogen chloride is bubbled through the reaction mixture, which is heated for 3 hours to 95°-100° C. and then concentrated, and the residue is diluted with water. The aqueous solution is extracted with ether, the ether is separated off and the aqueous layer is rendered alkaline with concentrated sodium hydroxide solution. The precipitate thus obtained is filtered off, washed with water and dried. Recrystallization from petroleum ether (60°-80° C.) gives 500 g of 1-methyl-3-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine of melting point 118°-122° C.

Workup

  1. temperaturethe temperature of the reaction mixture being maintained below 25° C
  2. additionAfter the addition
  3. customhydrogen chloride is bubbled through the reaction mixture, which
  4. temperatureis heated for 3 hours to 95°-100° C.
  5. concentrationconcentrated
  6. additionthe residue is diluted with water
  7. extractionThe aqueous solution is extracted with ether
  8. customthe ether is separated off
  9. customThe precipitate thus obtained
  10. filtrationis filtered off
  11. washwashed with water
  12. customdried
  13. customRecrystallization from petroleum ether (60°-80° C.)

Sources & evidence

ORD record
ord-1b6581a7b74e46498ba43ff2db01029a
Source dataset
uspto-grants-1990_02
Patent number
US04900727

Reaction notes

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