Benzaldehyde → 4-amino-5-chloro-N-((1-(5-dibenzylaminopentyl)piperidin-4-yl)methyl)-2-methoxybenzamide

HRID 344425Notes

Reaction equation

HRID 344425 reaction equation
[NH2:1][C:2]1[C:30]([Cl:31])=[CH:29][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][CH:26]=[CH:25][CH:24]=3)[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:32][CH3:33])[CH:3]=1.[CH:34](=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([BH3-])#N.[Na+]>>[NH2:1][C:2]1[C:30]([Cl:31])=[CH:29][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:14][CH2:15]2)=[O:7])=[C:4]([O:32][CH3:33])[CH:3]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 540154964-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 537045194-amino-5-chloro-N-((1-(5-dibenzylaminopentyl)piperidin-4-yl)methyl)-2-methoxybenzamideYield 22.7%

Procedure

4-Amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide (1.11 g) as starting compound, benzaldehyde (0.28 g) and sodium cyanoborohydride (0.33 g) were reacted and treated in the same manner as in Example 136 to give 0.3 g of 4-amino-5-chloro-N-((1-(5-dibenzylaminopentyl)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-b5270396d9b048a385d6c7b5120fd537
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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