Hexahydro-1,4-diazepine → 3-(1-Homopiperazinyl)-6-methoxy-1,2-benzisoxazole

HRID 1458552Notes

Reaction equation

HRID 1458552 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[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>CCOC(C)=O>[N:13]1([C:2]2[C:6]3[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=3[O:4][N:3]=2)[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 158169243-Chloro-6-methoxy-1,2-benzoxazole

Product 1

HCID 218393333-(1-Homopiperazinyl)-6-methoxy-1,2-benzisoxazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

3-Chloro-6-methoxy-1,2-benzisoxazole (5.0 g, 27.2 mml) and homopiperazine (8.2 g, 81.6 mmol) were combined and mechanically stirred under N2 at 140° C. for 45 minutes. The reaction mixture was cooled to room temperature, dissolved with EtOAc (500 ml), and the solution was washed with water, brine, dried over MgSO4, and concentrated in vacuo. Flash column chromatography (silica gel, 20% MeOH/CH2Cl2) provided the product (2.0 g, m.p. 74°-75° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washthe solution was washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customFlash column chromatography (silica gel, 20% MeOH/CH2Cl2) provided the product (2.0 g, m.p. 74°-75° C.

Sources & evidence

ORD record
ord-5349ea0088164e4990ed3ae3e7da87f2
Source dataset
uspto-grants-1998_12
Patent number
US05852022

Reaction notes

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