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

HRID 1525813Notes

Reaction equation

HRID 1525813 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-4192aefa9d6040db988050ddebda0fe9
Source dataset
uspto-grants-2015_07
Patent number
US09085563B2

Reaction notes

Loading…