Acetone → HCID 53711670, compound

HRID 582293Notes

Reaction equation

HRID 582293 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.[CH3:26][C:27]([CH3:29])=O.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][CH:27]([CH3:29])[CH3:26])=[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 180AcetoneHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 11110580HCID 11110580, compound

Product 1

HCID 53711670HCID 53711670, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

4-[1-(3-Amino-2-pyridyl)piperazin4-yl-carbonyl]benzoic acid methyl ester (4 g) was dissolved in methanol (90 ml) and then, acetone (2 ml), acetic acid (5 ml) and sodium cyanoborohydride (2.4 g) were added at 10° C. in order. The reaction mixture was stirred at 10° C. for 4 hours and heated to 20~25° C. and stirred for 1 hour. The solution was neutralized (pH=~8) by addition of aqueous 3N-sodium hydroxide, and excess of water was added gradually for precipitation. The mixture was stirred for 1 hour, filtered, washed with water, methanol and ether in order and dried to give 3.5 g (yield: 78%) of the desired compound as white crystal.

Workup

  1. temperatureheated to 20~25° C.
  2. stirringstirred for 1 hour
  3. stirringThe mixture was stirred for 1 hour
  4. filtrationfiltered
  5. washwashed with water, methanol and ether in order
  6. customdried

Sources & evidence

ORD record
ord-1ed1279a1c624907bfecac924b75026d
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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