2,2-Dipropyloxirane → 2-(3-(3-(2-Hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione

HRID 1189957Notes

Reaction equation

HRID 1189957 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[CH2:22]([C:25]1([CH2:28][CH2:29][CH3:30])[CH2:27][O:26]1)[CH2:23][CH3:24]>CCO.O>[OH:26][C:25]([CH2:28][CH2:29][CH3:30])([CH2:22][CH2:23][CH3:24])[CH2:27][NH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 134110112,2-DipropyloxiraneHCID 221249642-(3-(3-Aminophenyl)propyl)isoindoline-1,3-dione

Product 1

HCID 672991752-(3-(3-(2-Hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a stirred solution of 2-(3-(3-aminophenyl)propyl)isoindoline-1,3-dione (0.50 g, 1.78 mmol) in EtOH:H2O (9:1), 2,2-dipropyloxirane (0.45 g, 3.57 mmol) was added and the reaction mixture was stirred under reflux for 36 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (20% to 30% EtOAc—hexanes gradient) gave 2-(3-(3-(2-hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione as a yellow semisolid. Yield (0.22 g, 30%); 1H NMR (400 MHz, DMSO-d6) δ 7.86-7.81 (m, 4H), 6.92 (t, J=7.8 Hz, 1H), 6.45 (s, 1H), 6.41 (d, J=8.0 Hz, 1H), 6.37 (d, J=7.6 Hz, 1H), 4.89 (bs, 1H), 4.16 (s, 1H), 3.59 (t, J=7.2 Hz, 2H), 2.87 (d, J=5.2, 2H), 2.46-2.50 (m, 2H), 1.83-1.90 (quintet, J=7.2 Hz, 2H), 1.42-1.38 (m, 4H), 1.28-1.24 (m, 4H), 0.84 (t, J=7.2 Hz, 6H).

Workup

  1. temperatureunder reflux for 36 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customPurification by column chromatography (20% to 30% EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-c63d7e8e07b74a9097795b3483174c46
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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