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

HRID 2073285Notes

Reaction equation

HRID 2073285 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-f74347f3030743b2851e2537898cacce
Source dataset
uspto-grants-1990_04
Patent number
US04916150

Reaction notes

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