Lysergic Acid → Lysergic Acid N-ethyl N-(2-carbethoxy)ethyl Amide

A mixture of lysergic acid 5 (934 mg, 3.27 mmol) in 40 ml of dry dimethylformamide (DMF) was treated with 1,1′-carbonydidimidazole (CDI, 795 mg, 4.91 mmol) and stirred under nitrogen at room temperature for 1 hour. The N-ethyl N-(2-carbethoxy)ethyl amine linker 10 (1.90 g, 13.08 mmol) in 10 ml of dry dimethylformamide (DMF) was added dropwise and the reaction solution was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure and the resulting residue was dissolved in 200 ml of chloroform. The chloroform solution was washed twice with 100 ml of water, dried over anhydrous sodium sulphate, and concentrated under reduced pressure to yield the crude title compound 6 (2.2 g) as an oil. This was used without further purification in the following Example. υmax/cm−1 3121.90, 2987.10, 2848.65, 1735.30, 1676.97, 1202.97 (FT-IR: FIG. 9)

1. stirringthe reaction solution was stirred overnight at room temperature
2. concentrationThe reaction solution was concentrated under reduced pressure
3. dissolutionthe resulting residue was dissolved in 200 ml of chloroform
4. washThe chloroform solution was washed twice with 100 ml of water
5. dry with materialdried over anhydrous sodium sulphate
6. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-9fe6948392e045f8a8eb03a20c72f160

Quelldatensatz

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07115718B2