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

HRID 1292533Notes

Reaction equation

HRID 1292533 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-3690404aae75440aa5ca2b18109f860b
Source dataset
uspto-grants-1998_05
Patent number
US05756754

Reaction notes

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