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

HRID 1608301Notes

Reaction equation

HRID 1608301 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:19][C:20](OCC)=[O:21])[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH2:25]([N:27]([CH2:32][CH3:33])[CH2:28][CH2:29][CH2:30][NH2:31])[CH3:26]>>[CH2:25]([N:27]([CH2:32][CH3:33])[CH2:28][CH2:29][CH2:30][NH:31][C:20](=[O:21])[CH2:19][N:11]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:9]=[N:10]1)[CH3:26]

Participants

3

Reactant 2

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 14699557HCID 14699557, compound

Product 1

HCID 14699594N-[3-(Diethylamino)propyl]-4-(4-fluorophenyl)-5-phenyl-1H-pyrazole-1-acetamide

Procedure

A solution of 8.73 g (0.027 mol) of ethyl 4-(4-fluorophenyl)-5-phenyl-1H-pyrazole-1-acetate of example 7 in 30 mL of 3-(diethylamino)propanamine was heated at reflux for 3 hr. The excess amine was stripped under vacuum and the residue triturated in 1:1 hexane/methyl t-butyl ether. The solid was recrystallized from triethylamine to yield 8.4 g of product, mp 82°-83° C.

Workup

  1. temperatureat reflux for 3 hr
  2. customthe residue triturated in 1:1 hexane/methyl t-butyl ether
  3. customThe solid was recrystallized from triethylamine

Sources & evidence

ORD record
ord-a924cd174de94bab816dd2659b868193
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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