1-(2-Pyridyl)piperazine → 6-Methoxy-3-[1-(2-pyridyl)piperazinyl]-1,2-benzisoxazole

HRID 1292536Notes

Reaction equation

HRID 1292536 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=2[O:4][N:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CO>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([CH:20]3[CH2:21][NH:22][CH2:23][CH2:24][N:19]3[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=3)=[N:3][O:4][C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 944591-(2-Pyridyl)piperazineHCID 158169243-Chloro-6-methoxy-1,2-benzoxazole

Product 1

HCID 537029076-Methoxy-3-[1-(2-pyridyl)piperazinyl]-1,2-benzisoxazoleYield 34.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

A sealed tube was charged with 3-chloro-6-methoxy-1,2-benzisoxazole (0.25 g, 1.4 mmol) and 1-(2-pyridyl)piperazine (0.67 g, 4 mmol) and heated to 140° C. overnight. The reaction was cooled to room temperature, diluted with methanol, and concentrated in vacuo. The material was flash chromatographed (silica gel) eluting with CH2Cl2. The material was further purified through recrystallization from 1,2-dichloroethane/pet. ether to afford 0.15 g of the product, m.p.=123°-124° C.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customchromatographed (silica gel)
  4. washeluting with CH2Cl2
  5. customThe material was further purified through recrystallization from 1,2-dichloroethane/pet. ether

Sources & evidence

ORD record
ord-812fc5d7d83b4f0f940b7ff14613022c
Source dataset
uspto-grants-1998_05
Patent number
US05756754

Reaction notes

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