Dimethylformamide → (R)-2-(3-((3-Fluoro-4-morpholinophenyl)amino)-2-hydroxypropyl)isoindoline-1,3-dione

HRID 33741Notes

Reaction equation

HRID 33741 reaction equation
Cl[CH2:2][C@H:3]([OH:19])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:8]([F:18])[CH:7]=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[K].CN(C)C=O>O>[C:20]1(=[O:30])[N:24]([CH2:2][C@H:3]([OH:19])[CH2:4][NH:5][C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[C:8]([F:18])[CH:7]=2)[C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 16655948(2R)-1-Chloro-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-2-propanolHCID 24194345Phthalimide potassium salt

Product 1

HCID 16655949(R)-2-(3-((3-Fluoro-4-morpholinophenyl)amino)-2-hydroxypropyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of (N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline obtained in example 1, potassium phthalimide (40 gm) and Dimethyl formamide (400 ml) is heated for 5 hours at reflux temperature. The reaction mixture is cooled to ambient temperature, poured in to water (2 L) and filtered the solid obtained, and recrystallized from isopropyl alcohol to give 50 gm N-[3-pthalimido-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholinyl)aniline.

Workup

  1. temperatureis heated for 5 hours
  2. temperatureat reflux temperature
  3. filtrationfiltered the solid
  4. customobtained
  5. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-df20d167a6e64b09915674ff99213fbc
Source dataset
uspto-grants-2008_09
Patent number
US07429661B2

Reaction notes

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