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

HRID 1738779Notes

Reaction equation

HRID 1738779 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 mmol) 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-852631e9a6bc439ba2aae9eb060b3bb2
Source dataset
uspto-grants-1999_10
Patent number
US05965554

Reaction notes

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