Triethylamine → 6-[4-(4-phthalimidomethyl-piperidin-1-yl)-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone

HRID 1031474Notes

Reaction equation

HRID 1031474 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].Cl.[C:20]1(=[O:37])[N:24]([CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[C:23](=[O:32])[C:22]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:21]12.C(N(CC)CC)C>O1CCOCC1>[C:23]1(=[O:32])[N:24]([CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=4)=[CH:4][C:3]=3[N+:16]([O-:18])=[O:17])[CH2:30][CH2:31]2)[C:20](=[O:37])[C:21]2=[CH:36][CH:35]=[CH:34][CH:33]=[C:22]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28744326-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-oneHCID 144594952-((piperidin-4-yl)methyl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride

Product 1

HCID 144594966-[4-(4-phthalimidomethyl-piperidin-1-yl)-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.68 g (10 mmol) of 6-(4-chloro-3-nitro-phenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone and 2.81 g (10 mmol) of 4-phthalimidomethyl-piperidine hydrochloride are suspended in 30 ml of dioxane. After the addition of 2.8 ml (20 mmol) of triethylamine, the mixture is boiled under reflux for 4 hours. After it has cooled to room temperature, the solution is filtered from the residue and concentrated by evaporation under vacuum. After recrystallization of the solid residue from acetonitrile, 3.76 g (79%) of an orange yellow solid, m.p. 256°-258° C., are obtained.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationthe solution is filtered from the residue
  3. concentrationconcentrated by evaporation under vacuum
  4. customAfter recrystallization of the solid residue from acetonitrile, 3.76 g (79%) of an orange yellow solid, m.p. 256°-258° C.
  5. customare obtained

Sources & evidence

ORD record
ord-f5d1562439ff4cf9aa00268286dc2977
Source dataset
uspto-grants-1990_09
Patent number
US04954501

Reaction notes

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