Water → 2,3,4,4a,6,7,11b, 12,13,13a-decahydro-10-fluoro-1H-dibenzo[a,f]quinolizin-13-one

HRID 1576773Notes

Reaction equation

HRID 1576773 reaction equation
Cl.[F:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]=[CH:10]2)=[CH:5][CH:4]=1.[CH3:13][C:14]([C:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1)=[O:15].O>C(O)C>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][N:9]3[CH:10]([CH2:13][C:14](=[O:15])[CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]43)[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 136121-AcetylcyclohexeneHCID 203233233,4-Dihydro-7-fluoroisoquinoline hydrochloride

Product 1

HCID 203233112,3,4,4a,6,7,11b, 12,13,13a-decahydro-10-fluoro-1H-dibenzo[a,f]quinolizin-13-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 19.5 g (0.1 mole) of 3,4-dihydro-7-fluoroisoquinoline hydrochloride and 18.6 g (0.15 mole) of 1-cyclohexen-1-yl methyl ketone in 22 ml of ethanol is refluxed with stirring overnight then cooled to room temperature. The solution is poured into water, whereupon a suspension of undissolved material forms, and is extracted with ether. The aqueous layer and its suspended solid are stirred and treated with ammonium hydroxide solution to pH 8.5 to 9.0. The suspended solid is broken up, collected by decantation washed with water, dissolved in methylene chloride, dried over sodium sulfate and evaporated. The remaining residue is dissolved in benzene and chromatographed on alumina and eluted with benzene. The resulting solid is triturated with hexane and dried to give 2,3,4,4a,6,7,11b, 12,13,13a-decahydro-10-fluoro-1H-dibenzo[a,f]quinolizin-13-one, M.P. 130°-136°C.

Workup

  1. temperatureis refluxed
  2. extractionis extracted with ether
  3. stirringare stirred
  4. additiontreated with ammonium hydroxide solution to pH 8.5 to 9.0
  5. customcollected by decantation
  6. washwashed with water
  7. dissolutiondissolved in methylene chloride
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. dissolutionThe remaining residue is dissolved in benzene
  11. customchromatographed on alumina
  12. washeluted with benzene
  13. customThe resulting solid is triturated with hexane
  14. customdried

Sources & evidence

ORD record
ord-6d4a78d7665b4a31864616eb8a0d8c96
Source dataset
uspto-grants-1976_09
Patent number
US03983122

Reaction notes

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