Sodium Chloride → N-[3-(4-isopropyl-1-piperazinyl)propyl]phthalimide

HRID 1986164Notes

Reaction equation

HRID 1986164 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].[CH:16]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)([CH3:18])[CH3:17].C(N(C(C)C)CC)(C)C.[Na+].[Cl-]>O1CCOCC1.C(Cl)(Cl)Cl>[CH:16]([N:19]1[CH2:24][CH2:23][N:22]([CH2:2][CH2:3][CH2:4][N:5]2[C:9](=[O:10])[C:8]3[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]2=[O:15])[CH2:21][CH2:20]1)([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 21611N-3-BromopropylphthalimideHCID 780131-IsopropylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 20252235N-[3-(4-isopropyl-1-piperazinyl)propyl]phthalimideYield 88.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(3-Bromopropyl)phthalimide (16.7 g, 62.4 mmol) is added to a stirred solution of 1-isopropyl-piperazine (8.00 g, 62.4 mmol) and diisopropylethylamine (8.06 g, 62.4 mmol) in anhydrous 1,4-dioxane (300 mL). The resultant mixture is heated in an oil bath at 90° C. for 20 hours. At ambient temperature, chloroform (300 mL) and half-saturated aqueous NaCl (200 mL) are added to the mixture. The organic layer is separated, dried over magnesium sulfate, filtered, and concentrated. The crude oil is subjected to chromatography on silica gel and eluted with 2 M NH3/CH3OH in dichloromethane 0-5% to provide the title compound as a tan oil (17.4 g, 87% yield).

Workup

  1. customThe organic layer is separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluted with 2 M NH3/CH3OH in dichloromethane 0-5%

Sources & evidence

ORD record
ord-d70c2f5d6af64cf9aefdf6ec09a2e50e
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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