1-Acetylcyclopentene → 1,2,3,3a,5,6,10b,11,12,12a-Decahydro-8,9-dimethoxybenzo[a]cyclopenta[f]quinolizin-12-one

HRID 839513

Reaction equation

HRID 839513 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH:10]=[N:9][CH2:8][CH2:7]2.[CH3:16][C:17]([C:19]1[CH2:23][CH2:22][CH2:21][CH:20]=1)=[O:18]>C(O)C>[CH3:2][O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:11]2[CH:10]3[N:9]([CH2:8][CH2:7][C:6]=2[CH:5]=1)[CH:20]1[CH2:21][CH2:22][CH2:23][CH:19]1[C:17](=[O:18])[CH2:16]3

Participants

4

Reactant 2

HCID 1929251-AcetylcyclopenteneHCID 27246643,4-Dihydro-6,7-dimethoxyisoquinoline hydrochloride

Product 1

HCID 52186271,2,3,3a,5,6,10b,11,12,12a-Decahydro-8,9-dimethoxybenzo[a]cyclopenta[f]quinolizin-12-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 23.0 g (0.1 mole) of 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride, 23.0 g (0.2 mole) of 1-cyclopenten-1-yl methyl ketone in 25 ml of ethanol is refluxed overnight then evaporated in vacuo. The residual oil is partitioned between water and ether after which the aqueous layer is separated and washed with ether, made basic with concentrated ammonium hydroxide solution and stirred. A sticky solid material forms which is washed with water, partially dried in vacuo, dissolved in methylene chloride, dried over sodium sulfate, filtered and evaporated. The residual material is dissolved in benzene and chromatographed on alumina eluting with benzene then with benzene-15% ethyl acetate. The solid obtained is recrystallized from benzene-hexane to give 1,2,3,3a,5,6,10b,11,12,12a-decahydro-8,9-dimethoxybenzo[a]cyclopenta[f]quinolizin-12-one, M.P. 105°-114° C.

Workup

  1. temperatureis refluxed overnight
  2. customthen evaporated in vacuo
  3. customThe residual oil is partitioned between water and ether after which the aqueous layer
  4. customis separated
  5. washwashed with ether
  6. washA sticky solid material forms which is washed with water
  7. custompartially dried in vacuo
  8. dissolutiondissolved in methylene chloride
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. dissolutionThe residual material is dissolved in benzene
  13. customchromatographed on alumina eluting with benzene
  14. customThe solid obtained
  15. customis recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-3932c96dacd8410aaf57a0621e602967
Source dataset
uspto-grants-1978_06
Patent number
US04096147

Linked notes

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