Hydrochloric Acid → HCID 53838878, compound

HRID 1390263Notes

Reaction equation

HRID 1390263 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:12]N)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].O.Cl.C(O[CH:19](OCC)[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C:24]1=[O:29])C>C(O)C>[CH3:11][O:10][C:9]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[O:3][CH3:2])[NH:12][CH:19]=[C:20]2[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C:24]1=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 88490Hydrazine, (3,4-dimethoxyphenyl)-, hydrochlorideHCID 30173721-(4,4-Diethoxybutyl)piperidin-2-one

Product 1

HCID 53838878HCID 53838878, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

One dissolves 54 g of 3,4-dimethoxy phenylhydrazine hydrochloride in a mixture of 750 mls of ethanol, 750 mls of water and 350 mls of 5% hydrochloric acid. It is heated under a reflux, and then one adds over a period of 5 minutes a solution of 63 g of 1-(4,4-diethoxybutyl)-2-piperidone in 250 mls of ethanol. After heating under a reflux for 2 hours and then cooling, one eliminates the ethanol by distillation under reduced pressure (20 mm of mercury) and then extracts successively with 500 mls, 300 mls and 200 mls of methylene chloride. The combined organic phases are washed with 500 mls of water and then 500 mls of a saturated solution of sodium bicarbonate, dried over magnesium sulphate and evaporated to dryness under reduced pressure (20 mm of mercury). The residue (58 g) is chromatographed over 1 kg of silica gel contained in a column with a diameter of 6 cm, collecting fractions of 500 mls and eluting with ethyl acetate containing 1.5% of methanol. Fractions 31 to 43 are combined and evaporated to dryness. In this way one obtains 17 g of 1-[2(5,6-dimethoxy-3-indolyl) ethyl]-2-piperidone in the form of a thick yellow oil which slowly crystallises.

Workup

  1. temperatureIt is heated under a reflux
  2. temperatureAfter heating under
  3. temperaturea reflux for 2 hours
  4. temperaturecooling
  5. distillationby distillation under reduced pressure (20 mm of mercury)
  6. washThe combined organic phases are washed with 500 mls of water
  7. dry with material500 mls of a saturated solution of sodium bicarbonate, dried over magnesium sulphate
  8. customevaporated to dryness under reduced pressure (20 mm of mercury)
  9. customThe residue (58 g) is chromatographed over 1 kg of silica gel
  10. customcollecting fractions of 500 mls
  11. washeluting with ethyl acetate containing 1.5% of methanol
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-1ff8c84fbe634075b672b52334a34adb
Source dataset
uspto-grants-1979_02
Patent number
US04138489

Reaction notes

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