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A 100 mL round bottom flask was charged with 2-bromocyclohex-1-enecarbaldehyde, (prepared as described by Arnold, A. et. al. Collect. Czech. Chem. Commun., 1961, 26, 3059-3073.), (42 mmol), 4-piperazin-1-yl-benzoic acid ethyl ester (42 mmol) and ethanol (50 ml). The mixture was stirred and sodium cyanoborohydride (42 mmol) was added. Acetic acid was used to adjust pH to 5-6. The reaction mixture was stirred under N2 at room temperature overnight. The reaction mixture was filtered and washed with ethanol. The filtered solid was discarded and the combined organic layers were concentrated under vacuum. The mixture was purified by silica gel chromatography eluting with 5-10% ethyl acetate in hexanes to provide the title compound.

1. custom(prepared
2. customet. al. Collect
3. stirringThe reaction mixture was stirred under N2 at room temperature overnight
4. filtrationThe reaction mixture was filtered
5. washwashed with ethanol
6. concentrationthe combined organic layers were concentrated under vacuum
7. customThe mixture was purified by silica gel chromatography
8. washeluting with 5-10% ethyl acetate in hexanes