Methyl(2-(morpholin-4-yl)ethyl)amine → 6-Methoxy-N-methyl-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amine

HRID 1292508Notes

Reaction equation

HRID 1292508 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.[CH3:13][NH:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([N:14]([CH3:13])[CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[N:3][O:4][C:5]=2[CH:10]=1

Participants

3

Reactant 2

HCID 14979282Methyl(2-(morpholin-4-yl)ethyl)amineHCID 158169243-Chloro-6-methoxy-1,2-benzoxazole

Product 1

HCID 158169256-Methoxy-N-methyl-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amineYield 49.4%

Conditions

Temperature
140 °C

Procedure

To a sealed tube was added 3-chloro-6-methoxy-1,2-benzisoxazole (6.0 g) and N-methyl-N-[2-(4-morpholinyl)ethyl]-amine (13.8 g). The reaction was heated to 140° C. over 48 hours and then cooled to room temperature. The residue was partitioned between ethyl acetate (EtOAc) and water, extracted again with EtOAc, and the organic phase was dried over magnesium sulfate (MgSO4) and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 1% methanol/dichloromethane (MeOH/DCM) provided the product (4.7 g), m.p. 43°-44° C.

Workup

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

Sources & evidence

ORD record
ord-54df17111076414e98408f5517697d90
Source dataset
uspto-grants-1998_05
Patent number
US05756754

Reaction notes

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