Dimethylformamide → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]piperazine

https://huagongshe.com/de/reaction/10169

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Dimethylformamide	HCID 6228	—
Edukt	2-(3-Chloropropyl)-2-methyl-1,3-dioxolane	HCID 80079	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine	HCID 10972505	—
Lösungsmittel	Water	HCID 962	—
Produkt	(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]piperazine	HCID 58681859	40%

Reaktionsbedingungen

Temperatur	90 °C

Reaktionsschritte

A mixture of 5-chloro-2-pentanone ethylene ketal (0.54 g), (2R)-1-[3,5-bis(trifluoro-methyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (1.37 g), diisopropylethylamine (0.6 mL), and dimethylformamide (25 mL) was heated overnight, at 90°C. After cooling to room temperature the mixture was poured in water and extracted with ethyl acetate. The organic layer was dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 95/15) to afford (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]piperazine (0.7 g, 40%). MH+ 584.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US07094779B2
Quelldatensatz	uspto-grants-2006_08
ORD ID	ord-01898ff63c1d4a31a48358210ecd48cd
Quellennotiz	uspto-grants-2006_08