Benzamide, N-(4-hydroxybutyl)- → 6,7-Dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid (4-hydroxy-butyl)-amide

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([C:15](Cl)=[O:16])[CH2:7][CH2:6]2.[OH:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23]C(=O)C1C=CC=CC=1>>[OH:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:15]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:9]1)=[O:16]

Participants

Reactant 2

HCID 11217773Benzamide, N-(4-hydroxybutyl)-

HCID 798861106,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl chloride

Product 1

HCID 669375406,7-Dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid (4-hydroxy-butyl)-amideYield 67%

Procedure

6,7-Dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid (4-hydroxy-butyl)-amide (25B) is prepared from 25A as described for 1D.

Sources & evidence

ORD record: ord-b39c384e25c8491db227796022b2936c
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389555B2

Reaction notes

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