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

HRID 447322Notes

Reaction equation

HRID 447322 reaction equation
BrC1C=C[C:5]([N:8]2[CH2:13][C@H:12](C)[NH:11][C@H:10]([CH3:15])[CH2:9]2)=CC=1.I[C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1.CN(C)[C@H]1CCNC1>>[I:23][C:20]1[CH:21]=[CH:22][C:17]([N:11]2[CH2:10][CH2:15][C@H:13]([N:8]([CH3:5])[CH3:9])[CH2:12]2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 12208p-DiiodobenzeneHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 667303611-(4-Bromophenyl)-cis-3,5-dimethylpiperazine

Product 1

HCID 67446344(S)-1-(4-iodophenyl)-N,N-dimethylpyrrolidin-3-amine

Procedure

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.

Workup

  1. customThe title compound was purified by silica gel chromatography (MeOH/CH2Cl2, 2:98 to 1:9) as a yellow solid (1.27 g, 55%)

Sources & evidence

ORD record
ord-3462bbad00e04c7d94c1913a445e1638
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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