Piperidine → HCID 9965088, Verbindung

Temperatur

0 °C

The method was adapted from that reported for piperlonguminine (section 2.2) but utilising 3-benzo-1,3-dioxol-5-ylpropionic acid and piperidine as the acid and amine components respectively. A mixture of 3-benzo-1,3-dioxol-5-ylpropionic acid (200 mg, 0.0026 mole, 1 eq) and triethylarnine (0.27 ml, 0.002 mole, 2 eq) in dichloromethane (50 ml) was stirred for 15 min at 0° C. To this mixture methanesulfonyl chloride (0.11 ml, 0.0015 mole, 1.5 eq) was added and stirred for further 30 min at 0° C. Piperidine (0.15 ml, 0.0015 mole, 1.5 eq) was added to the mixture and stirred for 1 h at 0° C. and 1 h at room temperature. Dichloromethane (50 ml) was added to the mixture which was then washed with 5% HCl (3×100 ml), saturated aqueous NaHCO3 (3×100 ml) and water (3×100 ml). The organic fraction was dried over anhydrous sodium sulphate, filtered and rotary evaporated to yield brown oil (65% yield).

1. stirringstirred for further 30 min at 0° C
2. stirringstirred for 1 h at 0° C. and 1 h at room temperature
3. washwas then washed with 5% HCl (3×100 ml), saturated aqueous NaHCO3 (3×100 ml) and water (3×100 ml)
4. dry with materialThe organic fraction was dried over anhydrous sodium sulphate
5. filtrationfiltered
6. customrotary evaporated

ORD-Eintrag

ord-6488dad439dc46619654810f46e0a746

Quelldatensatz

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06346539B1