Acetaldehyde → 4-amino-5-chloro-N-((1-(6-(N-ethyl-N-(4-methoxybenzyl)amino)hexyl)-piperidin-4-yl)methyl)-2-methoxybenzamide

HRID 344432Notes

Reaction equation

HRID 344432 reaction equation
[NH2:1][C:2]1[C:33]([Cl:34])=[CH:32][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:35][CH3:36])[CH:3]=1.[CH:37](=O)[CH3:38].C([BH3-])#N.[Na+]>>[NH2:1][C:2]1[C:33]([Cl:34])=[CH:32][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:37][CH3:38])[CH2:23][C:24]3[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=3)[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:35][CH3:36])[CH:3]=1

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 539137474-amino-5-chloro-N-((1-(6-(4-methoxybenzylamino)hexyl)piperidin-4-yl)methyl)-2-methoxybenzamide

Product 1

HCID 538245924-amino-5-chloro-N-((1-(6-(N-ethyl-N-(4-methoxybenzyl)amino)hexyl)-piperidin-4-yl)methyl)-2-methoxybenzamide

Procedure

4-Amino-5-chloro-2-methoxy-N-((1-(6-(4-methoxybenzylamino)hexyl)-piperidin-4-yl)methyl)benzamide (0.9 g) as starting compound, acetaldehyde (0.12 ml) and sodium cyanoborohydride (0.26 g) were reacted and treated in the same manner as in Example 136 to give 0.55 g of 4-amino-5-chloro-N-((1-(6-(N-ethyl-N-(4-methoxybenzyl)amino)hexyl)-piperidin-4-yl)methyl)-2-methoxybenzamide.

Workup

  1. customwere reacted
  2. additiontreated in the same manner as in Example 136

Sources & evidence

ORD record
ord-183afe9dff15412dbfd6a5d2762f0b82
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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