1-Phenylpiperazine → HCID 70055762, compound

HRID 1977298Notes

Reaction equation

HRID 1977298 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=2)[CH:9]=1)=[O:4].[C:18]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>ClCCl.O1CCCC1.CO.C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:27]3[CH2:28][CH2:29][N:24]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:25][CH2:26]3)=[CH:12][CH:11]=2)[CH:9]=1)=[O:4]

Participants

9

Reactant 4

HCID 70961-PhenylpiperazineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 57286669HCID 57286669, compound

Product 1

HCID 70055762HCID 70055762, compoundYield 47.7%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-(4-formylphenyl)-1H-pyrazol-4-carboxylic acid methyl ester (5.0 g), 1-phenyl piperazine (4.21 g), acetic acid (3.7 ml), sodium cyanoborohydride (1.55 g), methanol (110 ml), tetrahydrofuran (75 ml) and dichloromethane (20 ml) was stirred for 15 minutes at 0° C. and for 14 hours at ambient temperature. The reaction mixture was poured into saturated NaHCO3 aqueous solution and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and evaporated. The residue was purified by silica gel chromatography (1:1 hexane-ethyl acetate elution) and recrystallized from diisopropyl ether and acetone to give 1-[4-(4-phenylpiperazin-1-yl-methyl)phenyl]-1H-pyrazol-4-carboxylic acid methyl ester (3.90 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography (1:1 hexane-ethyl acetate elution)
  6. customrecrystallized from diisopropyl ether and acetone

Sources & evidence

ORD record
ord-e4918e42e2ff4533b34b084b62725e66
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

Loading…