Potassium Carbonate → 1-[6,7-Dimethoxy-3,4-dihydro-2H-isoquinolin-1-one-2-yl]-3-[N-benzyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane

HRID 2164051Notes

Reaction equation

HRID 2164051 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])[C:9](=[O:15])[N:8]([CH2:16][CH2:17][CH2:18]Cl)[CH2:7][CH2:6]2.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl.CO>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[N:8]([CH2:16][CH2:17][CH2:18][N:32]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:31][CH2:30][C:24]1[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=1)[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 200274Benzyl-[2-(3,4-dimethoxy-phenyl)-ethyl]-amineHCID 133270272-(3-Chloropropyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-oneHCID 21584188Chloroform methanol

Product 1

HCID 227501191-[6,7-Dimethoxy-3,4-dihydro-2H-isoquinolin-1-one-2-yl]-3-[N-benzyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

1-[6,7-Dimethoxy-3,4-dihydro-2H-isoquinolin-1-one-2-yl]-3-[N-benzyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane was prepared analogous to Example 1 (b) by reacting 1-(6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one-2-yl)-3-chloropropane with N-(3,4-dimethoxy-phenylethyl)-N-benzyl-amine in chlorobenzene in the presence of potassium carbonate. Yield: 2.2 gm (69.8% of theory); Rf -value (chloroform/methanol = 19:1): 0.8.

Sources & evidence

ORD record
ord-f41b305cbcd346338a00ddcab60d224c
Source dataset
uspto-grants-1979_01
Patent number
US04137318

Reaction notes

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