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ChemicalBook CAS DataBase List Julolidine
479-59-4

Julolidine synthesis

4synthesis methods
Aniline

62-53-3

1,3-Propanediol

504-63-2

Julolidine

479-59-4

The general procedure for the synthesis of julolidine from aniline and 1,3-propanediol was as follows: aniline (1.0 mmol), IrCl3-3H2O (5.0 mol%, based on the amount of 1,3-propanediol), and rac-BINAP (7.5 mol%) were added to a reaction vial in air. Subsequently, homotrimethylbenzene (0.5 mL) and 1,3-propanediol (1.3 mmol) were added to the reaction vial and the reaction was stirred for 18 hours at 165 °C. After completion of the reaction, the reaction mixture was diluted with hexane and then filtered through filter paper. The filtrate was concentrated under vacuum and the resulting residue was purified by fast column chromatography on SiO2 (eluent ratio tBuOMe:hexane=1:15) to give 2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine as the final product.

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