6-Methyl-1,2,3,4-tetrahydroquinoline → 1-(3,4-Dimethoxybenzoyl)-2-methyl-4-(6-methyl-1,2,3,4-tetrahydroquinolin-1-yl)-1,2,3,4-tetrahydroquinoline

HRID 585371Notes

Reaction equation

HRID 585371 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11](O)[CH2:10][C@@H:9]1[CH3:19])=[O:7].[CH3:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH2:31][CH2:30][CH2:29]2>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([N:32]2[C:33]3[C:28](=[CH:27][C:26]([CH3:25])=[CH:35][CH:34]=3)[CH2:29][CH2:30][CH2:31]2)[CH2:10][CH:9]1[CH3:19])=[O:7]

Participants

3

Reactant 2

HCID 666786-Methyl-1,2,3,4-tetrahydroquinolineHCID 69774154cis-1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 223392471-(3,4-Dimethoxybenzoyl)-2-methyl-4-(6-methyl-1,2,3,4-tetrahydroquinolin-1-yl)-1,2,3,4-tetrahydroquinolineYield 18%

Procedure

Starting with cis-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol (500 mg, 1.53 mmol) prepared in Reference Example 1 and 6-methyl-1,2,3,4-tetrahydroquinoline (676 mg, 4.59 mmol), the same procedure as shown in Example 1 was repeated to give the titled compound (117 mg, yield: 18%) as a white crystal. (cis:trans=1.6:1)

Sources & evidence

ORD record
ord-2b619929ee1044739e70c78691b56694
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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