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0 °C

A solution of 3-bromo-6,7-dihydro-5H-[1]pyrindine (4 gm) and 3-chloroperoxybenzoic acid (2 equiv.) in CHCl3 was refluxed for 3 hours. An additional equivalent of 3-chloroperoxybenzoic acid was added to the reaction and heating was continued for another hour. The reaction was then cooled to 0° C., filtered, and extracted into CH2Cl2 from 1:1 saturated NaHCO3 /NaHCO3 (using caution), dried over Na2SO4, filtered, and evaporated. The residue was chromatographed on silica gel using 10:1 hexane/ethyl acetate to remove remaining starting material, ethyl acetate to remove 3-chloroperoxybenzoic acid residues, and then 10% MeOH/CH2Cl2 to elute the final compound. The product yield was 2 gm. 1H NMR(CDCl3): d 8.20 (s, 1 H), 7.25 (s, 1 H), 3.10 (m, 4 H), 2.20 (m, 2 H).

1. temperatureheating
2. waitwas continued for another hour
3. filtrationfiltered
4. extractionextracted into CH2Cl2 from 1:1 saturated NaHCO3 /NaHCO3 (using caution)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated
8. customThe residue was chromatographed on silica gel using 10:1 hexane/ethyl acetate
9. customto remove
10. customto remove 3-chloroperoxybenzoic acid residues
11. wash10% MeOH/CH2Cl2 to elute the final compound