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

HRID 344421Notes

Reaction equation

HRID 344421 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)[CH3:35].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][CH3:35])[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 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 540154964-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 540569734-amino-5-chloro-N-((1-(5-(N-ethyl-N-benzylamino)pentyl)piperidin-4-yl)methyl)-2-methoxybenzamide

Procedure

4-Amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide (1.46 g) as starting compound, acetaldehyde (0.19 ml) and sodium cyanoborohydride (0.43 g) were reacted and treated in the same manner as in Example 136 to give 0.8 g of 4-amino-5-chloro-N-((1-(5-(N-ethyl-N-benzylamino)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-3595ad60f0824f3c83ce437ef1f59763
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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