Potassium Iodide → 2-[2-(4-Pyridin-4-yl-piperazin-1-yl)-ethyl]-isoindole-1,3-dione

HRID 1663228Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:14][CH2:15][N:16]3[C:17](=[O:26])[C:18]4[C:19](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:21])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-pyridin-4-yl-piperazine [Org. Lett. 4 (2002) 737-740] (1.0 g, 6.12 mmol), N-(2-bromoethyl)-phthalimide (1.71 g, 6.74 mmol), potassium carbonate (0.85 g, 6.12 mmol), potassium iodide (1.02 g, 6.12 mmol) and dimethyl formamide (10 mL) was stirred at 70° C. for 24 h, then concentrated. The residue was dissolved in water, extracted with dichloromethane, the organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography using Kieselgel 60 (0.040-0.063 mm) (Merck) as adsorbent, and chloroform:methanol:NH4OH=10:1:0.1 as eluent to yield 1.52 g (74%) of the title compound, as a white solid.

Workup

concentrationconcentrated
dissolutionThe residue was dissolved in water
extractionextracted with dichloromethane
dry with materialthe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-670c0679107b4ad7b03aedcdd32e77ea
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034827B2

Reaction notes

Loading…