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

HRID 344393
Notes
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Reaction equation

HRID 344393 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[C:31]([Cl:32])=[CH:30][C:13]([C:14]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH2:29])[CH2:20][CH2:19]2)=[O:15])=[C:12]([O:33][CH3:34])[CH:11]=1.[BH4-].[Na+].O>C(O)C>[NH2:9][C:10]1[C:31]([Cl:32])=[CH:30][C:13]([C:14]([NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:22][CH2:23]2)=[O:15])=[C:12]([O:33][CH3:34])[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 4311764Sodium borohydrideHCID 540083634-Amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 540154964-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamideYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzaldehyde (0.76 g) was added to a solution of 4-amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (2.0 g) in ethanol (50 ml), and the mixture was stirred at refluxing temperature for 3 hr. Sodium borohydride (0.53 g) was added to the reaction mixture under ice-cooling, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia=50:5:1) to give 1.78 g of 4-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide.

Workup

  1. temperatureat refluxing temperature for 3 hr
  2. temperaturecooling
  3. stirringthe mixture was stirred overnight at room temperature
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia=50:5:1)

Sources & evidence

ORD record
ord-d8d6108f1b35472588e42ea8e4f89e05
Source dataset
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05864039

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes