Piperazine → HCID 53938946, compound

HRID 1725577Notes

Reaction equation

HRID 1725577 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C1CCN2C(=NCCC2)CC1>O>[N:12]1([C:2]2[C:6]3[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:5]=3[O:4][N:3]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 154539903-Chloro-5-methyl-1,2-benzoxazole

Product 1

HCID 53938946HCID 53938946, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Chloro-5-methyl-1,2-benzisoxazole (2.17 g, 12.93 mmol) was stirred together with piperazine (10.0 g, 116.1 mmol) and DBU (diazabicycloundecene; 2.0 g 13.14 mmol) in a melt at 120° C. for 4 h, after which the reaction was complete according to TLC. After cooling, the mixture was added to water, and the aqueous phase was extracted 3 times with dichloromethane, and the organic phases were washed with water, dried over magnesium sulfate and concentrated in vacuo. This resulted in 2.24 g of 3-piperazin-1-yl-5-methyl-1,2-benzisoxazole (yield: 80%) being obtained as a slightly impure solid product which was purified by chromatography.

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted 3 times with dichloromethane
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d8c63973cc04325ad7e94e8ae916a4d
Source dataset
uspto-grants-2009_02
Patent number
US07491729B2

Reaction notes

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