Formaldehyde → 6-[p-(3-(4-phenylpiperid-1-yl)-propionylamino)-phenyl]-4-methyl-3(2H)-pyridazinone

HRID 980200Notes

Reaction equation

HRID 980200 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH2:25][CH2:26][C:27](=[O:30])[NH:28][N:29]=4)=[CH:20][CH:19]=3)=[O:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:31]=O.[OH-].[K+]>C(O)C>[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:25]=[C:26]([CH3:31])[C:27](=[O:30])[NH:28][N:29]=4)=[CH:22][CH:23]=3)=[O:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 178135Altapizone

Product 1

HCID 221550016-[p-(3-(4-phenylpiperid-1-yl)-propionylamino)-phenyl]-4-methyl-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.0 g (10 millimoles) of 6-[p-(3-(4-phenylpiperid-1-yl)-propionylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone in 15 ml of ethanol were refluxed with 1.5 ml of 37% strength formalin solution and 40 ml of 4% strength ethanolic KOH for 3 hours. Insoluble material was filtered off under suction, after which the mother liquor was evaporated down and the product was recrystallized from isopropanol. 2.2 g of 6-[p-(3-(4-phenylpiperid-1-yl)-propionylamino)-phenyl]-4-methyl-3(2H)-pyridazinone were obtained as pale beige crystals of melting point 239°-240° C.

Workup

  1. filtrationInsoluble material was filtered off under suction
  2. customafter which the mother liquor was evaporated down
  3. customthe product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-ec48c9f4553344c99134a957fe303c23
Source dataset
uspto-grants-1987_01
Patent number
US04636504

Reaction notes

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