Acetaldehyde → 4-amino-5-chloro-N-((1-(5-(N-ethyl-N-(4-fluorobenzyl)amino)pentyl)-piperidin-4-yl)methyl)-2-methoxybenzamide

HRID 344412Notes

Reaction equation

HRID 344412 reaction equation
[NH2:1][C:2]1[C:31]([Cl:32])=[CH:30][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][NH:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:33][CH3:34])[CH:3]=1.[CH:35](=O)[CH3:36].C([BH3-])#N.[Na+]>>[NH2:1][C:2]1[C:31]([Cl:32])=[CH:30][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][N:21]([CH2:35][CH3:36])[CH2:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:33][CH3:34])[CH:3]=1

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 541377654-Amino-5-chloro-N-((1-(5-(4-fluorobenzylamino)pentyl)piperidin-4-yl)methyl)-2-methoxybenzamide

Product 1

HCID 543182164-amino-5-chloro-N-((1-(5-(N-ethyl-N-(4-fluorobenzyl)amino)pentyl)-piperidin-4-yl)methyl)-2-methoxybenzamide

Procedure

4-Amino-5-chloro-N-((1-(5-(4-fluorobenzylamino)pentyl)piperidin-4-yl)methyl)-2-methoxybenzamide (1.8 g) as starting compound, acetaldehyde (0.25 ml) and sodium cyanoborohydride (0.28 g) were reacted and treated in the same manner as in Example 136 to give 1.0 g of 4-amino-5-chloro-N-((1-(5-(N-ethyl-N-(4-fluorobenzyl)amino)pentyl)-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-0b1da6b4844e4da7a8549632c0aa9be9
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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