Piperazine → 6-Chloro-3-(piperazin-1-yl)benzo[d]isoxazole

HRID 241580Notes

Reaction equation

HRID 241580 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=2[O:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[OH-].[Na+]>>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[N:3][O:4][C:5]=2[CH:10]=1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 135684493,6-Dichlorobenzo[d]isoxazole

Product 1

HCID 135684516-Chloro-3-(piperazin-1-yl)benzo[d]isoxazoleYield 71.1%

Procedure

3,6-dichlorobenzisoxazole (5.2 g, 27.8 mmol), and anhydrous piperazine (24 g, 278 mmol) are placed in an egg type flask and react at 120° C. for 24 hours. After completion of the reaction, 52 ml of an ice-water mixture is added for quenching the reaction. Further 15 ml of 50% NaOH solution is added to the reaction solution. The reaction solution is stirred for 5 minutes and extracted with dichloromethane (30 ml×3). The dichloromethane layer is combined, washed with 20 ml of saturated saline, dried over anhydrous MgSO4, evaporated to dryness, and subjected to a separation on a column of alumina (200-300 mesh), eluting with dichloromethane:methanol-100:1, to obtain 4.7 g of 6-chloro-3-piperazinyl-benzisoxazole, with a yield of 71%.

Workup

  1. customreact at 120° C. for 24 hours
  2. additionis added
  3. customfor quenching
  4. customthe reaction
  5. extractionextracted with dichloromethane (30 ml×3)
  6. washwashed with 20 ml of saturated saline
  7. dry with materialdried over anhydrous MgSO4
  8. customevaporated to dryness
  9. customsubjected to a separation on a column of alumina (200-300 mesh)
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-736d716173fd49f089f5651ed616c9c1
Source dataset
uspto-grants-2014_02
Patent number
US08653069B2

Reaction notes

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