Triethylamine → 3-(4,5,6,7-Tetrafluoro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione

HRID 1866070Notes

Reaction equation

HRID 1866070 reaction equation
[CH2:1]1[CH:8]([NH2:9])[C:6](=[O:7])[NH:5][C:3](=[O:4])[CH2:2]1.Cl.Br[CH2:12][C:13]1[C:22]([F:23])=[C:21]([F:24])[C:20]([F:25])=[C:19]([F:26])[C:14]=1[C:15](OC)=[O:16].C(N(CC)CC)C>CN(C)C=O>[O:16]=[C:15]1[C:14]2[C:13](=[C:22]([F:23])[C:21]([F:24])=[C:20]([F:25])[C:19]=2[F:26])[CH2:12][N:9]1[CH:8]1[CH2:1][CH2:2][C:3](=[O:4])[NH:5][C:6]1=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 21928258HCID 21928258, compound

Product 1

HCID 129721383-(4,5,6,7-Tetrafluoro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 16.25 g of 2,6-dioxopiperidin-3-ammonium chloride, and 30.1 g of methyl 2-bromomethyl-3,4,5,6-tetrafluorobenzoate, and 12.5 g of triethylamine in 100 mL of dimethylformamide is stirred at room temperature for 15 hours. The mixture is then concentrated in vacuo and the residue mixed with methylene chloride and water. The aqueous layer is separated and back-extracted with methylene chloride. The combined methylene chloride solutions are dried over magnesium sulfate and concentrated in vacuo to give 1-oxo-2-(2,6-dioxopiperidin-3-yl)-4,5,6,7-tetrafluoroisoindoline.

Workup

  1. concentrationThe mixture is then concentrated in vacuo
  2. additionthe residue mixed with methylene chloride and water
  3. customThe aqueous layer is separated
  4. extractionback-extracted with methylene chloride
  5. dry with materialThe combined methylene chloride solutions are dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcbc68952843414caba0c01148519fc3
Source dataset
uspto-grants-2009_12
Patent number
US07629360B2

Reaction notes

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