Water → N-[3-(Diethylamino)propyl]-5-phenyl-4-(2-pyridinyl)-1H-pyrazole-1-acetamide

HRID 1650725Notes

Reaction equation

HRID 1650725 reaction equation
C(O[C:4](=[O:23])[CH2:5][N:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:8]=[N:7]1)C.[CH2:24]([N:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29][NH2:30])[CH3:25].O>CCOCC>[CH2:24]([N:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29][NH:30][C:4](=[O:23])[CH2:5][N:6]1[C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:8]=[N:7]1)[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 61011N,N-Diethyl-1,3-propanediamineHCID 15086050Ethyl-5-phenyl-4-(2-pyridinyl)-1H-pyrazole-1-acetate

Product 1

HCID 15086053N-[3-(Diethylamino)propyl]-5-phenyl-4-(2-pyridinyl)-1H-pyrazole-1-acetamideYield 43.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 10 g (0.032 mol) of ethyl 5-phenyl-4-(2-pyridinyl)pyrazole-1-acetate of example 1 in 15 mL (0.095 mol) of 3-(diethylamino)propanamine was heated at 100° for 3 hr. The excess amine was stripped in vacuo and the residue distributed between water and ether. The ether solution was dried over MgSO4, stripped and applied to 350 g of silica gel in a small amount of methylene chloride. The column was eluted with 20:1 acetone-triethylamine and a light yellow oil was obtained that crystallized upon triturating with cyclohexane to yield 5.4 g of product, mp 82°-83° C.

Workup

  1. dry with materialThe ether solution was dried over MgSO4
  2. washThe column was eluted with 20:1 acetone-triethylamine
  3. customa light yellow oil was obtained
  4. customthat crystallized
  5. customupon triturating with cyclohexane

Sources & evidence

ORD record
ord-66c898a6071d4bcba03c0ca47396bf10
Source dataset
uspto-grants-1990_05
Patent number
US04925857

Reaction notes

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