N,N-Diethyl-1,3-propanediamine → N-[3-(diethylamino)propyl]-4-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-1-acetamide

HRID 704831Notes

Reaction equation

HRID 704831 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([CH2:20][C:21]([O:23]CC)=O)[C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[CH2:26]([N:28]([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:29][CH3:30])[CH3:27]>>[CH2:26]([N:28]([CH2:29][CH3:30])[CH2:31][CH2:32][CH2:33][NH:34][C:21](=[O:23])[CH2:20][N:12]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:10]=[N:11]1)[CH3:27]

Participants

3

Reactant 2

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 14699555Ethyl 4-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-1-acetate

Product 1

HCID 14699593N-[3-(diethylamino)propyl]-4-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-1-acetamide

Procedure

A solution of 7.5 g (0.022 mol) of ethyl 4-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-1-acetate of example 4 in 35 mL of diethylaminopropylamine was stirred on a steam bath under nitrogen for 14 hours. The diethylaminopropylamine was removed in vacuo and the residue taken up in 200 mL of ethyl acetate. The ethyl acetate solution was washed twice with water, once with brine, and dried over sodium sulfate. The solvent was removed in vacuo and the residue was distilled in a Kugelrohr at 250° C./0.1 mm to yield 6.39 g of N-[3-(diethylamino)propyl]-4-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-1-acetamide as a clear viscous amber oil.

Workup

  1. customThe diethylaminopropylamine was removed in vacuo
  2. washThe ethyl acetate solution was washed twice with water, once with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo
  5. distillationthe residue was distilled in a Kugelrohr at 250° C./0.1 mm

Sources & evidence

ORD record
ord-92ff39f1a4d745a4a219c3d7e8d06a50
Source dataset
uspto-grants-1991_01
Patent number
US04988725

Reaction notes

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