反応 #926695

反応方程式

6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride

1-cyclopenten-1-yl methyl ketone

→

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

溶媒

ethanol

反応条件

後処理

1. 1
   温度is refluxed overnight
2. 2
   その他then evaporated in vacuo
3. 3
   その他The residual oil is partitioned between water and ether after which the aqueous layer
4. 4
   その他is separated
5. 5
   洗浄washed with ether
6. 6
   洗浄A sticky solid material forms which is washed with water
7. 7
   その他partially dried in vacuo
8. 8
   workup.DISSOLUTIONdissolved in methylene chloride
9. 9
   乾燥dried over sodium sulfate
10. 10
    ろ過filtered
11. 11
    その他evaporated
12. 12
    workup.DISSOLUTIONThe residual material is dissolved in benzene
13. 13
    その他chromatographed on alumina eluting with benzene
14. 14
    その他The solid obtained
15. 15
    その他is recrystallized from benzene-hexane

実験手順

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.

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