Triethylamine → 4-(4-Isopropyl-piperazin-1-yl)-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one

HRID 604266Notes

Reaction equation

HRID 604266 reaction equation
F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]2[C:3]=1[CH2:4][N:5]([CH3:15])[C:6]2=[O:14].C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.[CH:29]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)([CH3:31])[CH3:30]>CS(C)=O.O>[CH:29]([N:32]1[CH2:37][CH2:36][N:35]([C:2]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]3[C:3]=2[CH2:4][N:5]([CH3:15])[C:6]3=[O:14])[CH2:34][CH2:33]1)([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 780131-IsopropylpiperazineHCID 598492024-Fluoro-2-methyl-7-nitroisoindolin-1-one

Product 1

HCID 598492094-(4-Isopropyl-piperazin-1-yl)-2-methyl-7-nitro-2,3-dihydro-isoindol-1-oneYield 91%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 4-fluoro-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one (5.0 g, 24 mmol) and potassium carbonate (3.32 g, 24 mmol), triethylamine (6.7 mL, 28.8 mmol) in dimethylsulfoxide (50 mL), 1-isopropyl piperazine (4.1 mL, 28.8 mmol) is added and the mixture is stirred at 60° C. for 4 hours. The mixture is poured into iced water, and the resulting brown solids are collected by filtration and dried in vacuo at 50° C. to afford 4-(4-Isopropyl-piperazin-1-yl)-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one as brown solids in 91% yield. Rf=0.14 (AcOEt). 1H-NMR (400 MHz, CDCl3, δ, ppm): 1.09 (s, 3H), 1.11 (s, 3H), 2.70 (t, 4H), 2.80-2.74 (m, 1H), 3.19 (s, 3H), 3.21 (t, 4H), 4.37 (s, 2H), 7.01 (d, 1H), 7.78 (d, 1H).

Workup

  1. additionis added
  2. filtrationthe resulting brown solids are collected by filtration
  3. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-089c0b7f3c89404b9f31a40fad8c948f
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

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