N-Methylallylamine → (E)-allyl-[4-[4-(6-bromo-benzo[d]isoxazol-3-yl)-phenoxy]-but-2-enyl]-methyl-amine

HRID 342206

Reaction equation

BrC1C=CC2C(C3C=CC(O)=CC=3)=NOC=2C=1.BrC/C=C/CBr.[Br:24][C:25]1[CH:45]=[CH:44][C:28]2[C:29]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39]/[CH:40]=[CH:41]/[CH2:42]Br)=[CH:34][CH:33]=3)=[N:30][O:31][C:27]=2[CH:26]=1.[CH2:46]([NH:49][CH3:50])[CH:47]=[CH2:48]>>[CH2:46]([N:49]([CH2:42]/[CH:41]=[CH:40]/[CH2:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]2[C:28]3[CH:44]=[CH:45][C:25]([Br:24])=[CH:26][C:27]=3[O:31][N:30]=2)=[CH:33][CH:34]=1)[CH3:50])[CH:47]=[CH2:48]

Participants

Reactant 4

HCID 69391N-Methylallylamine

HCID 641245trans-1,4-Dibromo-2-butene

HCID 67596916(E)-6-bromo-3-[4-(4-bromo-but-2-enyloxy)-phenyl]-benzo[d]isoxazole

HCID 1363653254-(6-Bromo-benzo[d]isoxazol-3-yl)-phenol

Product 1

HCID 67598617(E)-allyl-[4-[4-(6-bromo-benzo[d]isoxazol-3-yl)-phenoxy]-but-2-enyl]-methyl-amine

Procedure

Analogously to Example 14d, from 4-(6-bromo-benzo[d]isoxazol-3-yl)-phenol and (E)-1,4-dibromo-2-butene via (E)-6-bromo-3-[4-(4-bromo-but-2-enyloxy)-phenyl]-benzo[d]isoxazole and by reaction with N-allyl-methyl-amine there is obtained (E)-allyl-[4-[4-(6-bromo-benzo[d]isoxazol-3-yl)-phenoxy]-but-2-enyl]-methyl-amine which is converted into the fumarate, MS: m/e 413 (M+H+, 1 Br).

Sources & evidence

ORD record: ord-5875efb8520d4946bac61c8e38102eda
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856503

Linked notes

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