N-3-Bromopropylphthalimide → 2-[3-(4-Methylpiperazin-1-yl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 1896075Notes

Reaction equation

HRID 1896075 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C1(C)C(C)=CC=CC=1>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:2][CH2:3][CH2:4][N:5]2[C:9](=[O:10])[C:8]3=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]3[C:6]2=[O:15])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 21611N-3-BromopropylphthalimideHCID 531671-Methylpiperazine

Product 1

HCID 202494272-[3-(4-Methylpiperazin-1-yl)propyl]-1H-isoindole-1,3(2H)-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of N-(3-bromopropyl)phthalimide (8.04 g, 30 mM) in xylene (60 mL) was added dropwise to a solution of 1-methylpiperazine (6.61 g, 66 mM) in xylene (90 mL) at 70° C. After the addition was complete, the mixture was heated under reflux for 20 hours. A precipitate was removed by filtration and the filtrate was concentrated. The crude product was purified by silica gel chromatography with 9:1 CH2Cl2:MeOH to give the product N-(3-(4-methylpiperazin-1-yl)propyl)phthalimide as an oil in 72% yield.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 20 hours
  4. customA precipitate was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by silica gel chromatography with 9:1 CH2Cl2

Sources & evidence

ORD record
ord-b057fa4a4614498aa67a844435d57ff2
Source dataset
uspto-grants-2013_08
Patent number
US08518885B2

Reaction notes

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