N-(1,2,3,4-tetrahydro-quinolin-6-yl)acetamide → N-[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-1,2,3,4-tetrahydroquinolin-6-yl]acetamide

HRID 585372Notes

Reaction equation

HRID 585372 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][C:31]([NH:35][C:36](=[O:38])[CH3:37])=[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[C:29](=[CH:30][C:31]([NH:35][C:36](=[O:38])[CH3:37])=[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 11745431N-(1,2,3,4-tetrahydro-quinolin-6-yl)acetamideHCID 69774154cis-1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 22339259N-[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-1,2,3,4-tetrahydroquinolin-6-yl]acetamideYield 7.1%

Procedure

Starting with cis-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol (350 mg, 1.07 mmol) prepared in Reference Example 1 and N-(1,2,3,4-tetrahydro-quinolin-6-yl)acetamide (475 mg, 2.50 mmol), the same procedure as shown in Example 1 was repeated to give the titled compound (38 mg, yield: 7%) as a colorless oil. (cis:trans=1:1.7)

Sources & evidence

ORD record
ord-1106d39f55ad4704a3a490cac15b693c
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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