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

HRID 839512Notes

Reaction equation

HRID 839512 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 reluxed 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 is 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 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. EXAMPLE 35

Workup

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

Sources & evidence

ORD record
ord-53ebfc730fcf4807a3fd08644f8b3716
Source dataset
uspto-grants-1978_06
Patent number
US04096147

Reaction notes

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