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. 2015 Dec 22;7(2):177–181. doi: 10.1021/acsmedchemlett.5b00357

Scheme 1. Synthesis of Compounds 17.

Scheme 1

Reagents and conditions: (a) 1-benzylpiperidin-4-amine, DMF, r.t.; (b) 3-chloro-2-(chloromethyl)prop-1-ene, NaH, THF; (c) hydroxylamine hydrochloride, Et3N, EtOH; (d) Raney nickel, H2, 30–50 psi, r.t.; (e) for 6 (y = 1), tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, DMF, r.t.; (f) for 7 (y = 2), tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate, DMF, r.t.; (g) TFA; (h) benzyl bromide, Et3N, DMF, r.t.