Acetonitrile → (4-Methyl-benzyl)-[3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl]-amine

HRID 8685

Reaction equation

HRID 8685 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1.C(#N)C>C(OCC)(=O)C.ClCCl>[CH3:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH:32][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]3[C:16]4[S:17][CH:18]=[CH:19][C:15]=4[O:14][N:13]=3)[CH:7]=2)=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 660354-MethylbenzylamineHCID 219835593-[3-(3-Bromo-propoxy)phenyl]-thieno[2,3-d]isoxazole

Product 1

HCID 21983594(4-Methyl-benzyl)-[3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl]-amineYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
75 °C

Procedure

Mix 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole (0.400 g, 1.18 mmol), potassium carbonate (0.326 g, 2.36 mmol), 4-methylbenzylamine (0.606, 5.00 mmol) and acetonitrile (5.0 mL) and heat (75° C.), overnight. Cool the reaction mixture and filter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate). Combine the appropriate fractions and concentrate to give a residue. Dissolved residue in 50% ethyl acetate in dichloromethane and chromatograph on silica (10 g) using ethyl acetate to give the title compound (356 mg, 80% yield). Purity by LC/MS (APCI)=98, [M+H]+=379.

Workup

  1. temperatureCool the reaction mixture
  2. filtrationfilter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate)
  3. concentrationCombine the appropriate fractions and concentrate
  4. customto give a residue

Sources & evidence

ORD record
ord-a99c1c0c4a2345f79a71dc7c55462a97
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Linked notes

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