1,2,3,4-Tetrahydroisoquinoline → 1-(3,4-Dimethoxybenzoyl)-2-methyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)-1,2,3,4-tetrahydroquinoline

HRID 585374Notes

Reaction equation

HRID 585374 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].[CH2:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][NH: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:26]2[CH2:27][CH2:28][C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:25]2)[CH2:10][CH:9]1[CH3:19])=[O:7]

Participants

3

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 69774154cis-1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 223392991-(3,4-Dimethoxybenzoyl)-2-methyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)-1,2,3,4-tetrahydroquinolineYield 39%

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-tetrahydroisoquinoline (487 mg, 3.66 mmol), the same procedure as shown in Example 1 was repeated to give the titled compound (210 mg, yield: 39%) as a white crystal. (cis:trans=1:1)

Sources & evidence

ORD record
ord-f75acd3ed05e4fbc918f5d34732bbb20
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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