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

HRID 613659Notes

Reaction equation

HRID 613659 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

A mixture of 3-chloro-6-methoxy-1,2-benzisoxazole (3.0 g) and piperazine (6.0 g) was heated to 140° C. over 4 hours in a sealed tube and then cooled to room temperature. The contents of the tube were dissolved in MeOH and further diluted with EtOAc (1 L). The precipitate 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 precipitate 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-10c0d819910d4fedb5bc3beac0171f8a
Source dataset
uspto-grants-1999_12
Patent number
US06008348

Reaction notes

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