Hydrazine → 1-(3-aminopropyl)-N,N-diethyl-D-lysergamide

Participants

Reaction Steps

A solution of 2.1 g (4.1 mmol) of 9 in 35 mL of methanol was treated with 0.92 mL (29.3 mmol) of anhydrous hydrazine and stirred at room temperature overnight. The reaction was concentrated at reduced pressure. The residue was diluted with 25 mL of methylene chloride, undissolved solids were filtered off, and the filtrate was chromatographed on 300 g of silica gel using 15% methanol in methylene chloride as eluent to remove front running impurities, then 2% triethylamine and 15% methanol in methylene chloride as eluent to elute the product to yield 1.24 g (79.5%) of 10 as a yellow amorphous solid.

Provenance & Evidence