Acetaldehyde → 4-[1-[3-(Ethylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid methyl ester

HRID 582295Notes

Reaction equation

HRID 582295 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1.[CH:26](=O)[CH3:27].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.O.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[C:23]([NH:24][CH2:26][CH3:27])=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:16][CH2:17]2)=[O:11])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 177AcetaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 11110580HCID 11110580, compound

Product 1

HCID 545122904-[1-[3-(Ethylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid methyl esterYield 81%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-[1-(3-Amino-2-pyridyl)piperazin-4-yl-carbonyl]benzoic acid methyl ester (4 g) was dissolved in methanol (80 ml) and then, acetaldehyde (1.7 ml) and acetic acid (4 ml) were added at 0° C. The solution was stirred at 0° C. for 30 minutes. Then, with the addition of sodium cyanoborohydride (2.2 g), the solution was stirred at 0~5° C. for 2 hours. Excess of water was added gradually, and the solution was neutralized (pH=~8) by addition of aqueous 3N-sodium hydroxide. The mixture was stirred for 1 hour and filtered, and the crude solid was recrystallized using methanol and ether to give 3.51 g (yield: 81%) of the desired compound.

Workup

  1. stirringthe solution was stirred at 0~5° C. for 2 hours
  2. stirringThe mixture was stirred for 1 hour
  3. filtrationfiltered
  4. customthe crude solid was recrystallized

Sources & evidence

ORD record
ord-18e9b4cfc6e74e2aabfe267fcf829463
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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