Trifluoroacetic acid → 3-(Pyrrolidin-1-yl)piperidine

Participants

Reaction Steps

The fumarate of the title compound of Example 5 (2.00 g, 5.40 mmol) was suspended in CHCl3 (20 mL) and the solution was treated with CF3COOH (25 mL). TLC (solvent system A) indicated the reaction to be complete after 10 min at rt. The solvent was evaporated in vacuo and the residue was dissolved in cold (5° C.) 50% aqueous NaOH (100 mL) and extracted with CHCl3 (2×100 mL). The combined organic layer was dried (Na2SO4) and the solvent was evaporated in vacuo to give the title compound (0.80 g, quantitative) as a colorless oil. The HBr salt of the title compound crustallized from 2-propanol: mp 217°-218° C.; 1H-NMR (CDCl3) ∂ 3.22 (dm, Jgem +11 Hz, 1H), 2.94 (dm, Jgem +12 Hz, 1H), 2.48-2.62 (complex m, 6H), 1.98-2.11 (complex m, 2H), 1.65-1.82 (complex m, 6H), 1.30-1.54 (complex m, 2H); CIMS (calcd for C9H18N2): 155. Found (MH+): 155; Anal. (calcd for C9H20Br2N2): C, H, N.

Provenance & Evidence