Piperidine → 2-[2-Hydroxy-3-(1-piperidinyl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 1192245Notes

Reaction equation

HRID 1192245 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(O)C>[OH:1][CH:2]([CH2:3][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 21601N-(2,3-Epoxypropyl)phthalimide

Product 1

HCID 602074632-[2-Hydroxy-3-(1-piperidinyl)propyl]-1H-isoindole-1,3(2H)-dioneYield 70.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(oxiran-2-ylmethyl)isoindoline-1,3-dione (1.0 g, 4.9 mmol) in ethanol (25 mL) was added piperidine (0.46 g, 5.4 mmol). The resulting reaction mixture was heated at reflux for 1 hour. After this time, TLC analysis showed no starting material remaining so the mixture was concentrated to afford the title product as oil (1.0 g). The titled product structure was confirmed by LC/MS analysis. MS m/z: 289.21 [M+H]+. The resulting hydroxylamine was dissolved in ethanol (20 mL) and to which was added hydrazine (0.86 g, 7.36 mmol). The resulting reaction mixture was stirred at ambient temperature for over night. After this time, TLC analysis showed no starting material remaining so the mixture was concentrated to afford the title product as oil (0.4 g). MS m/z: 159.2 [M+H]+. The crude was used as such for the next step transformation.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 1 hour
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-7463f035e82d4032920755a3cd8eff55
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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