Potassium Carbonate → [3-(3-Thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl]-thiophen-3-yl-methylamine

HRID 8649

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.ClCCCOC1C=C(C2[C:35]3[S:36][CH:37]=[CH:38][C:34]=3ON=2)C=CC=1.S1C=CC([CH2:44][NH2:45])=C1.C(=O)([O-])[O-].[K+].[K+]>>[O:14]1[C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:12]([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[O:5][CH2:4][CH2:3][CH2:2][N:45]([C:34]2[CH:38]=[CH:37][S:36][CH:35]=2)[CH3:44])=[N:13]1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 27763813-Thiophenemethylamine

HCID 219835563-[3-(3-Chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole

HCID 219835593-[3-(3-Bromo-propoxy)phenyl]-thieno[2,3-d]isoxazole

Product 1

HCID 69652986[3-(3-Thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl]-thiophen-3-yl-methylamineYield 86%

Procedure

The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-thiophenemethylamine and potassium carbonate essentially as described above in example 4. Combine the appropriate fractions and concentrate to give the title compound (0.32 g, 86% Yield) as an oil. Purity by LC/MS (APCI)=98%, [M+H]+=371 m/e.

Workup

concentrationCombine the appropriate fractions and concentrate

Sources & evidence

ORD record: ord-92bcf849b3e149aea25a639e139f430f
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091199B1

Linked notes

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