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

HRID 344417Notes

Reaction equation

HRID 344417 reaction equation
[NH2:1][C:2]1[C:29]([Cl:30])=[CH:28][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[S:24][CH:25]=[CH:26][CH:27]=3)[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1.[CH:33](=O)[CH3:34].C([BH3-])#N.[Na+]>>[NH2:1][C:2]1[C:29]([Cl:30])=[CH:28][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]([CH2:33][CH3:34])[CH2:22][C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)[CH2:14][CH2:15]2)=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 537599584-amino-5-chloro-2-methoxy-N-((1-(5-(2-thienylmethylamino)pentyl)piperidin-4-yl)methyl)benzamide

Product 1

HCID 541245674-amino-5-chloro-N-((1-(5-(N-ethyl-N-(2-thienylmethyl)amino)pentyl)-piperidin-4-yl)methyl)-2-methoxybenzamide

Procedure

4-Amino-5-chloro-2-methoxy-N-((1-(5-((2-thienylmethyl)amino)-pentyl)piperidin-4-yl)methyl)benzamide (1.5 g) as starting compound, acetaldehyde (0.23 ml) and sodium cyanoborohydride (0.25 g) were reacted and treated in the same manner as in Example 136 to give 0.96 g of 4-amino-5-chloro-N-((1-(5-(N-ethyl-N-(2-thienylmethyl)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-fc78a41443ad49d5816090a42b8afe15
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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