1,6-Dibromohexane → Allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-hexyl)-methyl-amine

HRID 342203Notes

Reaction equation

BrC1C=CC(C2C3C=CC(O)=CC=3ON=2)=CC=1.BrCCCCCCBr.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:49]=[CH:48][C:37]2[C:38]([C:41]3[CH:46]=[CH:45][C:44]([Br:47])=[CH:43][CH:42]=3)=[N:39][O:40][C:36]=2[CH:35]=1.[CH2:50]([NH:53][CH3:54])[CH:51]=[CH2:52]>>[CH2:50]([N:53]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:49]=[CH:48][C:37]2[C:38]([C:41]3[CH:46]=[CH:45][C:44]([Br:47])=[CH:43][CH:42]=3)=[N:39][O:40][C:36]=2[CH:35]=1)[CH3:54])[CH:51]=[CH2:52]

Participants

Reactant 4

HCID 123681,6-Dibromohexane

HCID 69391N-Methylallylamine

HCID 675982976-(6-Bromo-hexyloxy)-3-(4-bromo-phenyl)-benzo[d]isoxazole

HCID 1354908483-(4-Bromo-phenyl)-benzo[d]isoxazol-6-ol

Product 1

HCID 11729939Allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-hexyl)-methyl-amine

Procedure

Analogously to Example 12b, from 3-(4-bromo-phenyl)-benzo[d]isoxazol-6-ol and 1,6-dibromohexane via 6-(6-bromo-hexyloxy)-3-(4-bromo-phenyl)-benzo[d]isoxazole and by reaction with N-allyl-methyl-amine there is obtained allyl-[6-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-hexyl]-methyl-amine which is converted into the fumarate, MS: m/e 443 (M+H+, 1 Br).

Sources & evidence

ORD record: ord-02c1bed63ad64cb6aec438af82fee029
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856503

Reaction notes

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