6-Chloro-1,2,3,4-tetrahydroquinoline → 4-(6-Chloro-1,2,3,4-tetrahydroquinolin-1-yl)-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 585370Notes

Reaction equation

HRID 585370 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].[Cl: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>>[Cl:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH:11]1[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([C:6](=[O:7])[C:5]3[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]([CH3:19])[CH2:10]1)[CH2:31][CH2:30][CH2:29]2

Participants

3

Reactant 2

HCID 111828396-Chloro-1,2,3,4-tetrahydroquinolineHCID 69774154cis-1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 223392104-(6-Chloro-1,2,3,4-tetrahydroquinolin-1-yl)-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolineYield 37.1%

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 6-chloro-1,2,3,4-tetrahydroquinoline (614 mg, 3.66 mmol), the same procedure as shown in Example 1 was repeated to give the titled compound (216 mg, yield: 37%) as a colorless oil. (cis:trans=3.4:1)

Sources & evidence

ORD record
ord-80c043f453ad4dcfa05eadb2b98de974
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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