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

HRID 585359Notes

Reaction equation

HRID 585359 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].[NH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1>>[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:25]2[C:34]3[CH:29]([CH2:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][CH2:26]2)[CH2:10][CH:9]1[CH3:19])=[O:7]

Participants

3

Reactant 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 69774154cis-1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 697742481-(3,4-Dimethoxybenzoyl)-2-methyl-4-(tetrahydroquinolin-1-yl)-1,2,3,4-tetrahydroquinolineYield 40%

Procedure

Starting with cis-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol (400 mg, 1.22 mmol) prepared in Reference Example 1 and 1,2,3,4-tetrahydroquinoline (487 mg, 3.66 mmol), the same procedure as shown in Example 1 was repeated to give the product of interest, i.e., 1-(3,4-dimethoxybenzoyl)-2-methyl-4-(tetrahydroquinolin-1-yl)-1,2,3,4-tetrahydroquinoline (216 mg, yield: 40%) as a colorless oil. (cis:trans=1.6:1)

Sources & evidence

ORD record
ord-a8699756f996482e9b4d21b44b5358a8
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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