4-Nitrobenzyl chloride → 1-(4-Nitrobenzyl)piperidine

Participants

Reaction Steps

1-chloromethyl-4-nitro-benzene Compound 1i (5.0 g, 29 mmol) and piperidine (5.8 mL, 58 mmol) were combined in THF (30 mL) at ambient temperature. The reaction was refluxed for 4 hours, then diluted with aqueous 10% NH4Cl and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and evaporated in vacuo to provide 1-(4-nitro-benzyl)-piperidine Compound 1j (5.0 g) as a pale yellow oil requiring no further purification (see, Mitsuru Shiraishi, et al., J. Med. Chem., 2000, 43, 2049-2063). 1H NMR (DMSO-d6) δ 8.18 (d, 2H); 7.59 (d, 2H); 3.57 (s, 2H); 2.43-2.25 (m, 4H); 1.58-1.32 (m, 6H).

Provenance & Evidence