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

HRID 2396730Notes

Reaction equation

HRID 2396730 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 (11). 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-9c36a1c770a445859c3551dd8f1694b1
Source dataset
uspto-grants-1996_02
Patent number
US05494908

Reaction notes

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