Triethylamine → HCID 9816584, compound

HRID 2185950Notes

Reaction equation

HRID 2185950 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]([CH3:23])=[CH:21][CH:20]=[CH:19][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]([CH3:23])[CH:21]=[CH:20][CH:19]=2)[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 22455963HCID 22455963, compound

Product 1

HCID 9816584HCID 9816584, compound

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-methylbenzoate, 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-methylisoindoline.

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-b6f302ab8c8f4d0dab96f08a9fe91b9a
Source dataset
uspto-grants-2002_06
Patent number
US06403613B1

Reaction notes

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