2-{4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-hydroxybutyl}-1H-isoindole-1,3(2H)-dione → HCID 59296069, compound

HRID 2233369Notes

Reaction equation

HRID 2233369 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:13]([OH:27])[CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:8][CH2:7]1>C(O)C.NN>[NH2:16][CH2:15][CH2:14][CH:13]([OH:27])[CH2:12][N:9]1[CH2:8][CH2:7][CH:6]([O:5][C:4]2[CH:28]=[CH:29][C:30]([Cl:31])=[C:2]([Cl:1])[CH:3]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 592960492-{4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-hydroxybutyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59296069HCID 59296069, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 9321HydrazineSolvent

Procedure

A solution of mixture of 2-{4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-hydroxybutyl}-1H-isoindole-1,3(2H)-dione (3.00 g) in a mixture of ethanol (75 ml) and 35% aqueous hydrazine (15 ml) was heated at reflux 4 h. The mixture was cooled down and the solvents removed under vacuum. The residue was triturated with warm dichloromethane. The white solid was removed by filtration and the filtrate dried over sodium sulfate. The mixture was filtered and the solvent was evaporated to afford the title compound as a yellow oil (2.10 g) which was used without further purification in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux 4 h
  3. temperatureThe mixture was cooled down
  4. customthe solvents removed under vacuum
  5. customThe residue was triturated with warm dichloromethane
  6. customThe white solid was removed by filtration
  7. dry with materialthe filtrate dried over sodium sulfate
  8. filtrationThe mixture was filtered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-428c9bd6d8d746a9a58888bb410875e8
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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