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

HRID 839509Notes

Reaction equation

HRID 839509 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 3,4dihydroisoquinoline hydrochloride and 28.0 g (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 and concentrated to 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 to a solid which
  15. customis recrystallized from hexane-benzene

Sources & evidence

ORD record
ord-544c783c23ba4fe59633072304e15a71
Source dataset
uspto-grants-1978_06
Patent number
US04096147

Reaction notes

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