2-Propanone, 1-nitro- → 1,4-Dihydro-2,6-dimethyl-5-nitro-4-(2-trifluoromethylphenyl)-pyridine-3-carboxylic acid 4-cyclohexylpiperazide

HRID 580512Notes

Reaction equation

HRID 580512 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1C=CC=CC=1C=O.[N+:19]([CH2:22][C:23](=O)[CH3:24])([O-:21])=[O:20].[CH:26]1([N:32]2[CH2:37][CH2:36][N:35]([C:38](=[O:43])/[CH:39]=[C:40](\[NH2:42])/[CH3:41])[CH2:34][CH2:33]2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C(O)(C)C>[CH:26]1([N:32]2[CH2:33][CH2:34][N:35]([C:38]([C:39]3[CH:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:2]([F:1])([F:17])[F:18])[C:22]([N+:19]([O-:21])=[O:20])=[C:23]([CH3:24])[NH:42][C:40]=3[CH3:41])=[O:43])[CH2:36][CH2:37]2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 662962-Propanone, 1-nitro-HCID 13927252'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbaldehydeHCID 86742239HCID 86742239, compound

Product 1

HCID 867422401,4-Dihydro-2,6-dimethyl-5-nitro-4-(2-trifluoromethylphenyl)-pyridine-3-carboxylic acid 4-cyclohexylpiperazide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

17.4 g (0.10 mol) of 2-trifluoromethylphenylbenzaldehyde, 12.0 g (0.12 mol) of nitroacetone and 25.1 g (0.10 mol) of β-aminocrotonic acid 4-cyclohexylpiperazide are heated in 50 ml of isopropanol at 60° C. for 12 hours. On cooling, the product separates out and is recrystallized from isopropanol.

Workup

  1. temperatureOn cooling
  2. customis recrystallized from isopropanol

Sources & evidence

ORD record
ord-e7e4f18f80774170914c3b019461fcf8
Source dataset
uspto-grants-1988_06
Patent number
US04753936

Reaction notes

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