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

HRID 716776Notes

Reaction equation

HRID 716776 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-125179515e484f598769f15a8399438b
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

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