p-Diiodobenzene → N-(4-Iodophenyl)-N,N',N'-trimethylethane-1,2-diamine

HRID 447319Notes

Reaction equation

BrC1C=C[C:5]([N:8]2[CH2:13][C@H:12](C)[NH:11][C@H:10](C)[CH2:9]2)=CC=1.I[C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1.CN(C)CCNC>>[I:23][C:20]1[CH:21]=[CH:22][C:17]([N:11]([CH3:12])[CH2:10][CH2:9][N:8]([CH3:13])[CH3:5])=[CH:18][CH:19]=1

Participants

Reactant 3

HCID 12208p-Diiodobenzene

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-

HCID 667303611-(4-Bromophenyl)-cis-3,5-dimethylpiperazine

Product 1

HCID 67448628N-(4-Iodophenyl)-N,N',N'-trimethylethane-1,2-diamine

Procedure

The title compound was synthesized according to the synthesis of 1-(4-bromophenyl)-cis-3,5-dimethylpiperazine, except reacting 1,4-diiodobenzene (1.06 g, 3.21 mmol) with N,N,N′-trimethylethylenediamine (0.5 mL, 3.9 mmol). The title compound was purified by silica gel chromatography (MeOH/CH2Cl2, 5:95 to 1:5) to give a pale orange solid (0.62 g, 64%). 1H NMR (400 MHz, CDCl3) δ 7.50 (d, J=8.0 Hz, 2H), 6.55 (d, J=8.2 Hz, 2H), 3.77-3.76 (m, 2H), 2.99 (s, 3H), 2.99-2.92 (m, 2H), 2.65 (s, 6H); MS ESI 305.0 [M+H]+, calcd for [C11H17IN2+H]+ 305.04.

Workup

customThe title compound was purified by silica gel chromatography (MeOH/CH2Cl2, 5:95 to 1:5)

Sources & evidence

ORD record: ord-c4a725432b8342899ecdbb1ea6072c13
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481533B2

Reaction notes

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