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

HRID 582864

Reaction equation

HRID 582864 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-7a018fe6d1b2475e95ea4c203cd01652
Source dataset
uspto-grants-1999_07
Patent number
US05925766

Linked notes

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