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

HRID 839510

Reaction equation

HRID 839510 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.[CH3:12][C:13]([C:15]1[CH2:19][CH2:18][CH2:17][CH:16]=1)=[O:14]>C(O)C>[CH2:16]1[CH:15]2[CH:19]([N:3]3[CH:2]([CH2:12][C:13]2=[O:14])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4]3)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 1929251-AcetylcyclopenteneHCID 204638553,4-Dihydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 203232961,2,3,3a,5,6,10b,11,12,12a-Decahydrobenzo[a]cyclopenta[f]quinolizin-12-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 16.7 g (0.1 mole) of 3,4-dihydroisoquinoline hydrochloride and 27.0 g (0.02 mole) of 1-cyclopenten-1-yl methyl ketone in 22 ml of ethanol is refluxed overnight then evaporated to dryness. The remaining solid is dissolved in water and washed with ether. The aqueous layer is made basic with concentrated ammonium hydroxide solution with stirring. Upon the formation of an oil, ice is added to the mixture after which a solid is formed. The solid material is washed with water, dried overnight in a vacuum oven, and recrystallized from hexane to give 1,2,3,3a,5,6,10b,11,12,12 a-decahydrobenzo[a]cyclopenta[f]quinolizin-12-one, M.P. 101°-102.5° C.

Workup

  1. temperatureis refluxed overnight
  2. customthen evaporated to dryness
  3. dissolutionThe remaining solid is dissolved in water
  4. washwashed with ether
  5. additionUpon the formation of an oil, ice is added to the mixture after which a solid
  6. customis formed
  7. washThe solid material is washed with water
  8. customdried overnight in a vacuum oven
  9. customrecrystallized from hexane

Sources & evidence

ORD record
ord-f40f86d8c1224492954a95b4d2ab6fc0
Source dataset
uspto-grants-1978_06
Patent number
US04096147

Linked notes

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