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

HRID 447320Notes

Reaction equation

HRID 447320 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 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 667303611-(4-Bromophenyl)-cis-3,5-dimethylpiperazine

Product 1

HCID 66730449(R)-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 (R)—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 12:88) as a yellow solid (1.17 g, 51%). 1H NMR (400 MHz, MeOD) δ 7.42 (d, J=8.2 Hz, 2H), 6.39 (d, J=8.0 Hz, 2H), 3.51-3.47 (m, 1H), 3.44-3.39 (m, 1H), 3.29-3.24 (m, 1H), 3.13-3.09 (m, 2H), 3.00-2.87 (m, 1H), 2.35 (s, 6H), 2.35-2.26 (m, 1H), 1.96-1.86 (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 12:88) as a yellow solid (1.17 g, 51%)

Sources & evidence

ORD record
ord-57b08ec44a534953acdd55626e34bd64
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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