Hydrochloric Acid → HCID 22748828, compound

HRID 1390262Notes

Reaction equation

HRID 1390262 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.C(OC(OCC)[CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1=[O:25])C.[CH2:29](Cl)Cl>O.C(O)(=O)C>[CH3:2][O:3][C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[NH:10][CH:16]=[C:17]2[CH:18]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1=[O:25])[CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 77023(4-Methoxyphenyl)hydrazineHCID 30173721-(4,4-Diethoxybutyl)piperidin-2-one

Product 1

HCID 22748828HCID 22748828, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

One heats to 80° C a solution consisting of 140 mls of water, 60 mls of acetic acid and 40 mls of normal hydrochloric acid. One then adds 5.52 g of p-methoxyphenylhydrazine followed by 9.7 g of 1-(4,4-diethoxybutyl)-2-piperidone. The solution is maintained at 80° C for 2 hours. It is then cooled to 5° C and then one adds 200 mls of water and 150 mls of methylene chloride. After decanting, the aqueous phase is extracted again with 200 mls of methylene chloride. The organic phases are combined, washed with 100 mls of water and then with a saturated solution of sodium bicarbonate, dried over sodium sulphate, filtered over bleaching charcoal and then evaporated to dryness under reduced pressure (20 mm of mercury). The residue (10 g ) is chromatographed over 75 g of silica gel contained in a column with a diameter of 2.7 cm and eluting with ethyl acetate, collecting fractions of 120 mls. Fractions 4 to 12 are evaporated. In this way one obtains 7.5 g of 1[1(5-methoxy-3-indolyl)-ethyl]2-piperidone melting at 150° C. 1-(4,4-diethoxy-butyl)-2-piperidone may be prepared in the following manner:

Workup

  1. customheats to 80° C
  2. temperatureIt is then cooled to 5° C
  3. customAfter decanting
  4. extractionthe aqueous phase is extracted again with 200 mls of methylene chloride
  5. washwashed with 100 mls of water
  6. dry with materialwith a saturated solution of sodium bicarbonate, dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure (20 mm of mercury)
  9. customThe residue (10 g ) is chromatographed over 75 g of silica gel
  10. washeluting with ethyl acetate
  11. customcollecting fractions of 120 mls
  12. customFractions 4 to 12 are evaporated

Sources & evidence

ORD record
ord-c6903a74448c4d85a2e4e1c559e16f9c
Source dataset
uspto-grants-1979_02
Patent number
US04138489

Reaction notes

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