Formaldehyde → HCID 54704619, compound

Participants

Reaction Steps

To a stirred warm (60° C.) solution of ethyl 4-amino-1-piperidinecarboxylate (86.1 mg, 0.5 mmol) and paraformaldehyde (16 mg, 0.5 mmol) in methanol (2 mL) was added N-(3,4-dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (175 mg, 0.5 mmol). After 2 h, the reaction mixture was cooled and purified using preparative HPLC on a C18 column using water/methanol-(0.1% TFA) as the eluent. The fractions containing the desired product were combined, concentrated and lyophilized to give the title compound as a white powder (64 mg, 27% yield). 1HNMR (500 MHz, CDCl3) δ: 10.16 (2H, br s), 7.40 (1H, d, J=8.2 Hz), 7.35 (1H, s), 7.10 (1H, d, J=8.0 Hz), 4.59 (2H, s), 4.34–4.18 (3H, m), 4.13 (2H, q, J=7.0 Hz), 4.09 (2H, s), 2.06 (2H, s), 2.87–2.80 (2H, br m), 1.82–1.76 (2H, br m), 1.63–1.55 (2H, m), 1.25 (3H, t, J=7.0 Hz). MS calcd for C21H26Cl2N3O5 (M+H): 470.36. found: 470.02.

Provenance & Evidence