3-Chloro-1,2-benzoxazole → N-methyl-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amine

HRID 1003328Notes

Reaction equation

HRID 1003328 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[CH3:11][NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>>[CH3:11][N:12]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1

Participants

3

Reactant 2

HCID 27797803-Chloro-1,2-benzoxazoleHCID 14979282Methyl(2-(morpholin-4-yl)ethyl)amine

Product 1

HCID 15453429N-methyl-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amineYield 23.5%

Conditions

Temperature
140 °C

Procedure

To a sealed tube was added 3-chloro-1,2-benzisoxazole (3.0 g) and N-methyl-N-[2-(4-morpholinyl)ethyl]-amine (12.7 g). The reaction was heated to 140° C. over 72 hours and then cooled to room temperature. The residue was partitioned between EtOAc and water, extracted again with EtOAc, and the organic phase was dried over MgSO4 and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 1-3% MeOH/DCM provided the product (1.2 g), as an oil.

Workup

  1. temperaturecooled to room temperature
  2. customThe residue was partitioned between EtOAc and water
  3. extractionextracted again with EtOAc
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washFlash column chromatography (silica gel) eluting with 1-3% MeOH/DCM

Sources & evidence

ORD record
ord-01538e2561c94a6a81fa7035cfae266f
Source dataset
uspto-grants-2000_04
Patent number
US06046203

Reaction notes

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