Sodium Carbonate → 3-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol

HRID 1080417Notes

Reaction equation

HRID 1080417 reaction equation
C[O:2][C:3]1[CH:21]=[CH:20][C:6]2[C:7]([N:10]([CH3:19])[CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:8][O:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+]>Br>[N:13]1([CH2:12][CH2:11][N:10]([CH3:19])[C:7]2[C:6]3[CH:20]=[CH:21][C:3]([OH:2])=[CH:4][C:5]=3[O:9][N:8]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 158169256-Methoxy-N-methyl-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amine

Product 1

HCID 1358150583-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-olYield 90%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

6-Methoxy-N-methyl-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amine (7.0 g) was dissolved in 48% hydrobromic acid (130 ml) and heated to reflux under nitrogen for 3 hours. The reaction was cooled to room temperature, neutralized with saturated sodium carbonate (Na2CO3) extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo. Flash chromatography (silica gel) eluting with 2:1 heptane/acetone provided the product (6.0 g), m.p. 91°-92° C.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 3 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography (silica gel) eluting with 2:1 heptane/acetone

Sources & evidence

ORD record
ord-5c6d82be2343416788cd839330fc3487
Source dataset
uspto-grants-1996_12
Patent number
US05580982

Reaction notes

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