Water → 2,3,4,4a,6,7,11b,12,13,13a-decahydro-12-methyl-1H-dibenzo[a,f]-quinolizin-13-one

HRID 1576770Notes

Reaction equation

HRID 1576770 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]=1.[CH2:12]([C:14]([C:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1)=[O:15])[CH3:13].O>C(O)C>[CH3:13][CH:12]1[CH:2]2[N:3]([CH2:4][CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=32)[CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]2[C:14]1=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 5730111-Propanone, 1-(1-cyclohexen-1-yl)-HCID 204638553,4-Dihydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 203232972,3,4,4a,6,7,11b,12,13,13a-decahydro-12-methyl-1H-dibenzo[a,f]-quinolizin-13-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 16.75 g (0.1 mole) of 3,4-dihydroisoquinoline hydrochloride and 28.0 g of (0.2 mole) of 1-cyclohexen-1-yl ethyl ketone in 28 ml of ethanol is refluxed for 52 hours then poured into 300 ml of water and extracted with ether. The aqueous layer is separated and made basic by slowly adding ammonium hydroxide solution with stirring. Stirring is continued until a solid is formed after which the liquid is decanted. The solid is washed with water, dissolved in methylene chloride, dried over sodium sulfate and concentrated to an oil. The oil is dissolved in refluxing hexane, filtered, concentrated and cooled to give a solid which is recrystallized from hexane-benzene to give 2,3,4,4a,6,7,11b,12,13,13a-decahydro-12-methyl-1H-dibenzo[a,f]quinolizin-13-one, M.P. 144.5°-147.5°C.

Workup

  1. temperatureis refluxed for 52 hours
  2. extractionextracted with ether
  3. customThe aqueous layer is separated
  4. stirringStirring
  5. customis formed after which the liquid
  6. customis decanted
  7. washThe solid is washed with water
  8. dissolutiondissolved in methylene chloride
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated to an oil
  11. dissolutionThe oil is dissolved
  12. temperaturein refluxing hexane
  13. filtrationfiltered
  14. concentrationconcentrated
  15. temperaturecooled
  16. customto give a solid which
  17. customis recrystallized from hexane-benzene

Sources & evidence

ORD record
ord-bc7b67eea96841258f1c8d0e398ea7f5
Source dataset
uspto-grants-1976_09
Patent number
US03983122

Reaction notes

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