Sodium Iodide → (+/-)-Methyl(cis)-1-[2,5-bis(trifluoromethyl)benzyl]-2-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

(±)-Methyl(cis)-2-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate (Example (18b) (88 mg), 2,5-bis(trifluoromethyl)benzyl bromide (110 mg), NaI (25 mg) and K2CO3 (100 mg) in DMF (3 ml) were placed in a microwave tube and the contents were heated in the microwave oven for 20 min at 150° C. The cooled mixture was dispersed between water and EtOAc and the organic extracts were washed with sodium thiosulfate, brine, dried (MgSO4) and evaporated. The crude oil was purified by chromatography on silica using 5-8% EtOAc in hexane to yield a colourless oil (98 mg, 62%) which crystallized on standing. 1H NMR (400 MHz, CDCl3) δ: 1.81-1.89 (2H, m), 1.97 (1H, d, J 13.2), 2.09-2.17 (2H, m), 2.49-2.56 (1H, m), 2.94-2.96 (1H, m), 3.34 (1H, d, J 15.6), 3.40 (1H, dd, J 2.6, 11.3), 3.66 (4H, d, J 15.6), 7.53-7.59 (5H, m), 7.68 (1H, d, J 8.2), 8.19 (1H, s); M/Z (ES+) 514 (MH+).

Provenance & Evidence