(+-)-p-Methoxyamphetamine → 1-(p-Methoxyphenyl)-2-propanone

HRID 6758

Reaction equation

HRID 6758 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH2:12])[CH3:11])=[CH:5][CH:4]=1.[CH3:13][CH:14]1[CH2:23][C:22]2[C:17](=[CH:18][C:19]([OH:24])=[CH:20][CH:21]=2)[CH2:16][NH:15]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([CH2:9][CH2:10][NH:12][CH2:13]2)=[CH:7][CH:8]=1.[CH2:16]1[C:17]2[C:22](=[CH:21][CH:20]=[C:19]([OH:24])[CH:18]=2)[CH2:23][CH2:14][NH:15]1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:24])[CH3:11])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 31721(+-)-p-MethoxyamphetamineHCID 220185193-Methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

Product 3

HCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 4172887-Methoxy-1,2,3,4-TetrahydroisoquinolineHCID 4192681,2,3,4-Tetrahydroisoquinolin-7-ol

Procedure

7-Methoxy-1,2,3,4-tetrahydro-isoquinoline and 1,2,3,4-tetrahydro-isoquinolin-7-ol were prepared by a literature procedure (J. Med. Chem. 1987, 30, 2208–2216). 2-(4-Methoxy-phenyl)-1-methyl-ethylamine required for the preparation of 3-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol was obtained from 1-(4-methoxy-phenyl)-propan-2-one by Procedure X and was subsequently converted to the tetrahydroisoquinoline by the same literature method.

Sources & evidence

ORD record
ord-f405ed59b2104cc7a767f0e2836109f2
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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