Potassium Carbonate → 4-amino-5-chloro-2-methoxy-N-((1-(6-(N-methyl-N-phenylamino)hexyl)piperidin-4-yl)-methyl)benzamide

HRID 344444Notes

Reaction equation

HRID 344444 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:9])=[C:6]([O:21][CH3:22])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:29][N:30]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]Cl)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][N:30]([CH3:29])[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:16][CH2:17]2)=[O:9])=[C:6]([O:21][CH3:22])[CH:5]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 540929106-(N-methyl-N-phenylamino)hexyl chlorideHCID 699663304-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride

Product 1

HCID 544507024-amino-5-chloro-2-methoxy-N-((1-(6-(N-methyl-N-phenylamino)hexyl)piperidin-4-yl)-methyl)benzamideYield 70.3%

Procedure

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (1.3 g) as starting compound, potassium carbonate (2.0 g) and 6-(N-methyl-N-phenylamino)hexyl chloride (0.8 g) were reacted and treated in the same manner as in Example 168 to give 1.2 g of 4-amino-5-chloro-2-methoxy-N-((1-(6-(N-methyl-N-phenylamino)hexyl)piperidin-4-yl)-methyl)benzamide.

Workup

  1. customwere reacted
  2. additiontreated in the same manner as in Example 168

Sources & evidence

ORD record
ord-593f328afbf640f0b9dc8fae29399d43
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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