Water → 2-{2-[1-(2-Fluoro-4-nitrophenyl)piperidin-4-yl]ethyl}isoindoline-1,3-dione

HRID 2241908Notes

Reaction equation

[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[N:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:25][CH2:24]1.O>CN(C)C=O>[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[N:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH2:25][CH2:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium phthalimide (0.580 g, 4.68 mmol) was added to a solution of toluene-4-sulfonic acid 2-[1-(2-fluoro-4-nitrophenyl)piperidin-4-yl]ethyl ester (compound of Reference Example 65; 0.661 g, 1.56 mmol) in N,N-dimethylformamide (10 ml), and the mixture was stirred at 80° C. for 1 hour. Water was added to the reaction mixture, and the precipitated solid was collected by filtration and washed with water to give the title compound (0.577 g, 93%) as a yellow solid.

Workup

filtrationthe precipitated solid was collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-55e558b33a9443288484ded2c37c9e4f
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671058B2

Reaction notes

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