N-Methylallylamine → (E)-allyl-[4-[1-(4-bromo-phenyl)-3,4-dihydro-isoquinolin-6-yloxy]-but-2-enyl]-methyl-amine

HRID 342219

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[CH2:11][CH2:10][N:9]=2)=[CH:4][CH:3]=1.Br[CH2:20]/[CH:21]=[CH:22]/[CH2:23]Br.[CH2:25]([NH:28][CH3:29])[CH:26]=[CH2:27]>>[CH2:25]([N:28]([CH2:20]/[CH:21]=[CH:22]/[CH2:23][O:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[C:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[N:9][CH2:10][CH2:11]2)[CH3:29])[CH:26]=[CH2:27]

Participants

Reactant 3

HCID 69391N-Methylallylamine

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

HCID 1359807951-(4-Bromo-phenyl)-3,4-dihydro-isoquinolin-6-ol

Product 1

HCID 67597954(E)-allyl-[4-[1-(4-bromo-phenyl)-3,4-dihydro-isoquinolin-6-yloxy]-but-2-enyl]-methyl-amine

Procedure

Analogously to Example 25, from 1-(4-bromo-phenyl)-3,4-dihydro-isoquinolin-6-ol and (E)-1,4-dibromo-2-butene and after reaction with N-allyl-methyl-amine there is obtained (E)-allyl-[4-[1-(4-bromo-phenyl)-3,4-dihydro-isoquinolin-6-yloxy]-but-2-enyl]-methyl-amine, which is converted into the fumarate, MS: m/e 425 (M+H+, 1 Br).

Sources & evidence

ORD record: ord-92f1078f453840168843e77f32032a66
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856503

Linked notes

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