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A mixture of 3.3 g (11 mmole) of 2-bromo-4,5,6-trimethoxy-1-indanone (Haworth et al., J. Chem. Soc. 1952 1583-1588), 2.16 g (10 mmole) of 1-(1-oxo-3-phenyl-2-propenyl)-piperazine, 0.92 g (11 mmole) of NaHCO3 in 8 ml of methanol is refluxed with stirring for 16 hours. After cooling, and maintaining the temperature at 0°-5° C., 0.77 g (20 mmole) of NaBH4 are added at portions, then the mixture is allowed to stand for 4 hours at room temperature under stirring. The mixture is cooled and made acidic by the addition of 15% aqueous HCl. After concentration under reduced pressure, the mixture is made alkaline by the addition of an aqueous 5% solution of sodium carbonate and extracted with methylene dichloride. The organic phase is washed with H2O to neutrality and dried over sodium sulfate. On evaporation under reduced pressure, 4.2 g are obtained as a mixture of diastereoisomers cis/trans which are separated by flash-chromatography through a column filled with silicagel 60 Merck 230-400 mesh, using chloroform:acetone 50:50 as the eluent. After crystallization from acetone, 1,2 g of cis-isomer are obtained (yield 27.4%), m.p. 162-163° C. On cristallization from acetone, 1.25 g of trans-isomer are obtained (yield 28.5%); m.p. 168°-170° C.

1. temperatureis refluxed
2. temperatureAfter cooling
3. temperaturemaintaining the temperature at 0°-5° C.
4. waitto stand for 4 hours at room temperature
5. stirringunder stirring
6. temperatureThe mixture is cooled
7. concentrationAfter concentration under reduced pressure
8. additionby the addition of an aqueous 5% solution of sodium carbonate
9. extractionextracted with methylene dichloride
10. washThe organic phase is washed with H2O to neutrality
11. dry with materialdried over sodium sulfate
12. customOn evaporation under reduced pressure, 4.2 g
13. customare obtained as a mixture of diastereoisomers cis/trans which
14. customare separated by flash-chromatography through a column
15. additionfilled with silicagel 60 Merck 230-400 mesh
16. customAfter crystallization from acetone, 1,2 g of cis-isomer
17. customare obtained (yield 27.4%), m.p. 162-163° C