p-Diiodobenzene → (S)-1-(4-iodophenyl)-N,N-dimethylpyrrolidin-3-amine

Participants

Reaction Steps

The title compound was synthesized according to the synthesis of 1-(4-bromophenyl)-cis-3,5-dimethylpiperazine, except reacting 1,4-diiodobenzene (2.41 g, 7.30 mmol) with (S)—N,N-dimethylpyrrolidin-3-amine (1.0 g, 8.8 mmol). The title compound was purified by silica gel chromatography (MeOH/CH2Cl2, 2:98 to 1:9) as a yellow solid (1.27 g, 55%). 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=8.7 Hz, 2H), 6.33 (d, J=8.0 Hz, 2H), 3.47-3.38 (m, 2H), 3.32-3.26 (m, 1H), 3.16-3.12 (m, 1H), 2.89-2.83 (m, 1H), 2.33 (s, 6H), 2.26-2.21 (m, 1H), 1.99-1.89 (m, 1H); MS ESI 317.0 [M+H]+, calcd for [C12H17IN2+H]+ 317.04.

Provenance & Evidence