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

HRID 1608288Notes

Reaction equation

HRID 1608288 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:18][C:19]([O:21]CC)=[O:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:24]([N:26]([CH2:29][CH2:30][CH2:31][NH2:32])[CH2:27][CH3:28])[CH3:25]>CCOCC>[OH2:20].[CH2:24]([N:26]([CH2:27][CH3:28])[CH2:29][CH2:30][CH2:31][NH:32][C:19](=[O:21])[CH2:18][N:10]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[N:9]1)[CH3:25].[CH2:24]([N:26]([CH2:29][CH2:30][CH2:31][NH:32][C:19](=[O:21])[CH2:18][N:10]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[N:9]1)[CH2:27][CH3:28])[CH3:25]

Participants

4

Reactant 2

HCID 61011N,N-Diethyl-1,3-propanediamine2×HCID 146995514,5-Diphenyl-1-(ethoxycarbonylmethyl)-pyrazole

Product 1

HCID 67948083N-[3-(diethylamino)propyl]-4,5-diphenyl-1H-pyrazole-1-acetamide hemihydrateYield 82.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 8 g (0.026 mol) of ethyl 4,5-diphenyl-1H-pyrazole-1-acetate (Example) and 40 mL (0.25 mol) of diethylaminopropylamine was heated on a steam bath under nitrogen for 14 hours. The excess diethylaminopropylamine was stripped in vacuo and the residue dissolved in ether. The ether solution was washed two times with water, once with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting white residue was dissolved in ether and a small amount of undesired material was removed by filtration after addition of some pentane. The filtrate was stripped, redissolved in ether, dried over magnesium sulfate, treated with decolorizing carbon, filtered and evaporated. The resulting residue was triturated in water, filtered and rinsed with water to yield 8.55 g (82%) of N-[3-(diethylamino)propyl]-4,5-diphenyl-1H-pyrazole-1-acetamide hemihydrate, mp 70°-74° C. The product can be recrystallized from wet ether.

Workup

  1. temperaturewas heated on a steam bath under nitrogen for 14 hours
  2. washThe ether solution was washed two times with water
  3. dry with materialonce with saturated sodium chloride, dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. dissolutionThe resulting white residue was dissolved in ether
  7. customa small amount of undesired material was removed by filtration
  8. additionafter addition of some pentane
  9. dissolutionredissolved in ether
  10. dry with materialdried over magnesium sulfate
  11. additiontreated with decolorizing carbon
  12. filtrationfiltered
  13. customevaporated
  14. customThe resulting residue was triturated in water
  15. filtrationfiltered
  16. washrinsed with water

Sources & evidence

ORD record
ord-3a75bb94c4654d2c868eca2bb319b208
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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