Diethylamine → 2-(1-(2-Hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione 2-(diethylamino)acetate

HRID 475029Notes

Reaction equation

HRID 475029 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[OH:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[CH2:13][CH2:12][CH:11]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[C:10]1=[O:27].C(=O)([O-])[O-].[K+].[K+].C(NCC)C>CN(C=O)C>[CH2:8]([N:9]([CH2:10][CH3:11])[CH2:2][C:3]([OH:5])=[O:4])[CH3:7].[OH:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[CH2:13][CH2:12][CH:11]([N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[C:10]1=[O:27]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 866187532-(1-(2-Hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione bromoacetate

Product 1

HCID 692485852-(1-(2-Hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione 2-(diethylamino)acetateYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1-(2-hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione bromoacetate (409 mg) was dissolved in DMF (10 mL). Potassium carbonate powder (800 mg) was added. Diethylamine solution (0.4 mL) was added dropwise while stirring. The reaction mixture was stirred for 24 hrs at room temperature. The solvent and the residual diethylamine were removed by rotary evaporation in vacuo. The resultant solid mixture was subjected to silica gel column chromatography (eluted with acetic ether:petroleum ether=2:1) and then a white solid (128 mg) was obtained. 1H NMR (CDCl3, ppm) δ 7.87-7.90 (m, 2H), 7.76-7.79 (m, 2H), 4.97-5.04 (m, 1H), 4.28-4.33 (m, 2H), 4.08-4.16 (m, 2H), 3.30 (s, 2H), 2.97-3.02 (m, 1H), 2.76-2.85 (m, 2H), 2.61-2.68 (m, 4H), 2.10-2.14 (m, 1H), 1.02-1.06 (m, 6H). MS (m/e): 416 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred for 24 hrs at room temperature
  2. customThe solvent and the residual diethylamine were removed by rotary evaporation in vacuo
  3. washThe resultant solid mixture was subjected to silica gel column chromatography (eluted with acetic ether:petroleum ether=2:1)

Sources & evidence

ORD record
ord-d9ead6c635e945509114dcb53e539823
Source dataset
uspto-grants-2014_01
Patent number
US08637545B2

Reaction notes

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