Hydrochloric Acid → HCID 66650706, compound

Participants

Reaction Conditions

Reaction Steps

2-(piperazin-1-yl)ethyl 4-phenylpiperazine-1-carboxylate (None HCl salt of Example 30; 291 mg, 0.91 mmol) was dissolved in DMF (2 mL). Iodoethane (74 μl, 2.31 mmol) and DIPEA (0.3 mL, 1.72 mmol) were added and the reaction mixture was heated at 170° C. for 15 minutes in a Biotage Initiator microwave at high absorption and then concentrated in vacuo. The residue was dissolved in 1 M aq Na2CO3 solution (25 mL) and extracted with DCM (3×25 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified normal phase column chromatography (eluting with DCM, followed by a 200:8:1 mixture of DCM:EtOH:NH3) followed by reverse phase chromatography (gradient eluting with MeOH in water, with 1% formic acid in each solvent, 0-100%) to give a colourless oil. The oil was dissolved in DCM, treated with an excess of 2M HCl in Et2O and concentrated in vacuo to give 2-(4-ethylpiperazin-1-yl)ethyl 4-phenylpiperazine-1-carboxylate trihydrochloride (197 mg, 52%) as a white solid.

Provenance & Evidence