Piperazine → 6-Methoxy-3-(1-piperazinyl)-1,2-benzisoxazole hemihydrate

HRID 1080439Notes

Reaction equation

HRID 1080439 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.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>CO.CCOC(C)=O>[OH2:4].[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:3][O:4][C:5]=2[CH:10]=1.[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:3][O:4][C:5]=2[CH:10]=1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 158169243-Chloro-6-methoxy-1,2-benzoxazole

Product 1

HCID 699469126-Methoxy-3-(1-piperazinyl)-1,2-benzisoxazole hemihydrate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a sealed tube was added 3-chloro-6-methoxy-1,2-benzisoxazole (3.0 g) and piperazine (6.0 g). The reaction was heated to 140° C. over 4 hours and then cooled to room temperature. The residue was dissolved in MeOH and further diluted with EtOAc (1 l). The precipatate was filtered and the filtrate dried over MgSO4 and concentrated in vacuo. Flash chromatography (silica gel) eluting with 30% MeOH/EtOAc provided a residue upon evaporation (3.6 g), m.p. 79°-80° C.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipatate was filtered
  3. dry with materialthe filtrate dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washFlash chromatography (silica gel) eluting with 30% MeOH/EtOAc
  6. customprovided a residue
  7. customupon evaporation (3.6 g), m.p. 79°-80° C.

Sources & evidence

ORD record
ord-4e85b2331d52415399ba439ad55ef56a
Source dataset
uspto-grants-1996_12
Patent number
US05580982

Reaction notes

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