Acetaldehyde → HCID 53708651, compound

HRID 344408Notes

Reaction equation

HRID 344408 reaction equation
[CH:1](=O)[CH3:2].[C:4]([BH3-])#[N:5].[Na+].[NH2:8][C:9]1[C:30]([Cl:31])=[CH:29][C:12]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]N)[CH2:19][CH2:18]2)=[O:14])=[C:11]([O:32][CH3:33])[CH:10]=1.[OH-].[Na+].[CH3:36]O>>[NH2:8][C:9]1[C:30]([Cl:31])=[CH:29][C:12]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:5]([CH2:4][CH3:36])[CH2:1][CH3:2])[CH2:19][CH2:18]2)=[O:14])=[C:11]([O:32][CH3:33])[CH:10]=1

Participants

6

Reactant 5

HCID 177AcetaldehydeHCID 887MethanolHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 540083634-Amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 53708651HCID 53708651, compound

Procedure

Acetaldehyde (0.32 ml) and sodium cyanoborohydride (0.36 g) were added to a solution of 4-amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (1.0 g) in methanol (20 ml), and the mixture was stirred at room temperature for 1 hr. A 10% aqueous sodium hydroxide solution 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=5:1) to give 0.55 g of 4-amino-5-chloro-N-((1-(5-diethylaminopentyl)piperidin-4-yl)methyl)-2-methoxybenzamide.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-95aca08f75d64847ab6ab1525adeb91a
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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