Potassium Carbonate → 8-(6,7-diethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-octanoic acid benzyloxyamide

HRID 392113Notes

Reaction equation

HRID 392113 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:21]([O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][C:33]=1[O:34][CH2:35][CH3:36])[CH2:30][NH:29][CH2:28][CH2:27]2)[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:29]1[CH2:28][CH2:27][C:26]2[C:31](=[CH:32][C:33]([O:34][CH2:35][CH3:36])=[C:24]([O:23][CH2:21][CH3:22])[CH:25]=2)[CH2:30]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113364038-Bromo-octanoic acid benzyloxyamideHCID 162322366,7-Diethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 865914278-(6,7-diethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-octanoic acid benzyloxyamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner analogous to that of example 1(b), 8-bromo-octanoic acid benzyloxy-amide (example 1(a); 0.38 g, 1.2 mmol) was reacted with 6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.3 g, 1.2 mmol) in the presence of potassium carbonate (0.16 g, 1.2 mmol) and DMF as solvent to give 8-(6,7-diethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-octanoic acid benzyloxyamide as an almost colorless wax (yield 0.15 g, 27%; purified by column chromatography using silica gel and ethyl acetate: methanol=9:1 as an eluent). MS (M+H+)=469.

Sources & evidence

ORD record
ord-3e50e4b67c8e4688a35e40d5a9a47b3c
Source dataset
uspto-grants-2004_10
Patent number
US06800638B2

Reaction notes

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