3-Chloromethyl-2-(3,4,5-trimethoxyphenyl)pyridine → 4-[N-(3,4-Methylenedioxyphenyl)-N-[[2-(3,4,5-trimethoxypheny)pyridin-3-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine Trihydrochloride

HRID 2300339Notes

Reaction equation

HRID 2300339 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:23]=[CH:22][N:21]=[C:20]([C:24]5[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=5)[CH:19]=4)[CH2:13][CH2:12]3)=[CH:4][C:3]=2[O:2]1.[Cl:36][CH2:37][C:38]1[C:39]([C:44]2[CH:49]=[C:48]([O:50][CH3:51])[C:47]([O:52][CH3:53])=[C:46]([O:54][CH3:55])[CH:45]=2)=[N:40][CH:41]=[CH:42][CH:43]=1>>[ClH:36].[ClH:36].[ClH:36].[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([N:10]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:23]=[CH:22][N:21]=[C:20]([C:24]5[CH:25]=[C:26]([O:34][CH3:35])[C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=5)[CH:19]=4)[CH2:13][CH2:12]3)[CH2:37][C:38]3[C:39]([C:44]4[CH:49]=[C:48]([O:50][CH3:51])[C:47]([O:52][CH3:53])=[C:46]([O:54][CH3:55])[CH:45]=4)=[N:40][CH:41]=[CH:42][CH:43]=3)=[CH:4][C:3]=2[O:2]1

Participants

3

Reactant 2

HCID 120431463-Chloromethyl-2-(3,4,5-trimethoxyphenyl)pyridineHCID 120434874-(3,4-Methylenedioxyphenylamino)-1-[[2-(3,4,5-trimethoxyphenyl) pyridin-4-yl]methyl]piperidine

Product 1

HCID 224611754-[N-(3,4-Methylenedioxyphenyl)-N-[[2-(3,4,5-trimethoxypheny)pyridin-3-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine Trihydrochloride

Procedure

4-(3,4-Methylenedioxyphenylamino)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine (119 mg) and 3-chloromethyl-2-(3,4,5-trimethoxyphenyl)pyridine (114 mg) were condensed in the same manner as described in Example 9. Yellow syrup obtained was converted to a trihydrochloroide to give the title compound as yellow powder.

Workup

  1. customcondensed in the same manner
  2. customYellow syrup obtained

Sources & evidence

ORD record
ord-81dd5f43b17d45d9bc10855d2463e228
Source dataset
uspto-grants-2002_12
Patent number
US06498169B1

Reaction notes

Loading…