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Synthesis of 5-MeO-DIPT from indole

William Dampier

Active member

The appropriate 5-MeO-indole (100 g) was dissolved in 1500 ml anhydrous ether and stirred on ice for 30 min. Oxalyl chloride (325 g) was added dropwise, stirred for 30 min on ice and kept at -20 *C for 4 h. The orange a-oxo acid chlorides filtered and washed three times with 50 ml cold anhydrous ether and dried in vacuum for 3 h at room temperature to give a yield of 148 g.


Diisopropylamine (170 g) was added dropwise to an ice-cold solution of 5-Methoxyindole-3-yl-glyoxalylchloride (100 g) dissolved in 1500 ml anhydrous THF. The mixture was stirred on ice for 4 h. The solvent was evaporated under reduced pressure to give a crude yellow solid 126 g.


A solution of the glyoxalylamide (100 g), in 1000ml anhydrous THF, was added dropwise to a stirred, ice-cold slurry of lithium aluminium hydride (125 g) in 500 ml anhydrous THF. This reaction mixture was refluxed for 15 h and then cooled on ice. The excess hydride was destroyed by the dropwise addition of 1100 ml water, followed by 1100 ml 20% NaOH and 1100 ml of water. The precipitated inorganic salts were filtered and washed 3 times with 500 ml THF. The filtrate was evaporated under reduced pressure and the resulting oily residue was dissolved in 750 ml DCM and washed three times with water and once with saturated aq. NaCl. The organic phase was dried over anhydrous MgSO4 and evaporated under reduced pressure. The resulting colourless transparent oils were dried overnight under vacuum over P2O5 to yield 79 g of a beige solid base.

5-MeO-DIPT (10 g) free base was dissolved in 100 ml anhydrous ether. Dry gaseous HCl was passed through the solution. After filtration, 9,74 g of pink hydrochloride salt was obtained that was washed three times with 50 ml anhydrous ether and dried in vacuum for 3 h. Recrystallisation with isopropanol yielded colourless 5-MeO-DIPT-HCl crystals.
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