Water → N-[3-(Diethylamino)Propyl]-4-Phenyl-1H-Pyrazole-1-Acetamide

HRID 477466Notes

Reaction equation

HRID 477466 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][C:13]([O:15]CC)=O)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([N:20]([CH2:25][CH3:26])[CH2:21][CH2:22][CH2:23][NH2:24])[CH3:19].O>CN(C=O)C>[CH2:18]([N:20]([CH2:25][CH3:26])[CH2:21][CH2:22][CH2:23][NH:24][C:13](=[O:15])[CH2:12][N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[N:9]1)[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 61011N,N-Diethyl-1,3-propanediamineHCID 14772168ethyl 4-phenyl-1H-pyrazole-1-acetate

Product 1

HCID 14772169N-[3-(Diethylamino)Propyl]-4-Phenyl-1H-Pyrazole-1-AcetamideYield 19.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 13.5g (0.059 mol) of ethyl 4-phenyl-1H-pyrazole-1-acetate of example 3 and 12.6 mL (0.08 mol) of 3-(diethylamino)propanamine in 130 mL of DMF was stirred at 100° C. for 4hr. The reaction was poured into water, extracted into methlene chloride, and stripped. The residue was triturated in ether and the resulting solid was recrystallized from ether-hexane to yield 3.70g of product, mp 55°-57° C.

Workup

  1. extractionextracted into methlene chloride
  2. customThe residue was triturated in ether
  3. customthe resulting solid was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-7f93ab8813164db185911a1c01c218ee
Source dataset
uspto-grants-1989_12
Patent number
US04888352

Reaction notes

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