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30th March 2011 @ 06:35
Racemization experiments on S-(+)-PZQamine with Raney nickel under high pressure and high temperature. Continuation of: Racemization of S-(+)-PZQamine with Raney Nickel (MW50-6, MW50-7)

Scheme MW50-6.png

See also:
Racemization of S-(+)-PZQamine with Pd/C (MW50-1 to MW50-3)
Racemization of S-(+)-PZQamine with Pd/C (MW50-4)
Racemization of S-(+)-PZQamine with Pd/BaSO4 (MW50-5)
Thiyl radical-mediated racemization of S-(+)-PZQamine (MW50-8)

Hazard and Risk Assessment:
HRAF MW50.pdf

Start time: 10:00 AM 30/03/2011
End time: 18:00 PM 30/03/2011

To a solution of S-(+)-PZQamine (50 mg, 248 µmol, MW: 202.3 g/mol) in ethanol (40 mL, minimum volume of the high pressure vessel) was added Raney nickel (29 µL suspension of Raney nickel in water (~0.1 g/mL), 2.91 mg, 49.5 µmol, 20 mol%, M.W. (Ni) 58.7 g/mol) under hydrogen pressure (10 bar, 150 psi) and heated to 100°C for 6 h.
- problem with the heating: temperature went up to 210°C and a pressure of ~ 500 psi (33 bar).

TLC (ethyl acetate, methanol, triethylamine, 1:1:0.02, stain: ninhydrin, reference: rac-PZQamine):

TLC (ethyl acetate, methanol, triethylamine, 10:1:0.02, stain: KMnO4 / ninhydrin):
TLC MW50-10 + MW50-11.JPG
Attached Files
1H NMR MW50-11 (crude).pdf
TLC MW50-10 + MW50-11.JPG