Hydrazine hydrate (1:1) → Altapizone

HRID 980203Notes

Reaction equation

HRID 980203 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:30]=[CH:29][C:21]([C:22]([CH2:24][CH2:25][C:26](O)=[O:27])=O)=[CH:20][CH:19]=3)=[O:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:32][NH2:33]>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:30]=[CH:29][C:21]([C:22]4[CH2:24][CH2:25][C:26](=[O:27])[NH:32][N:33]=4)=[CH:20][CH:19]=3)=[O:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 221549993-{p-[3-(4-Phenylpiperidino)propionylamino]-benzoyl}-propionic acid

Product 1

HCID 178135Altapizone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (23.7 millimoles) of 3-{p-[3-(4-phenylpiperidino)-propionylamino]-benzoyl}-propionic acid were stirred with 1.2 g (23.7 millimoles) of hydrazine hydrate in 200 ml of ethanol for 5 hours at 80° C. The product was filtered off under suction and recrystallized from dimethylformamide/water. 7.6 g (78%) of 6-{p-[3-(4-phenylpiperidino)-propionylamino]-phenyl}-4,5-dihydro-3(2H)-pyridazinone.1/4H2O were obtained as colorless crystals of melting point 238°-240° C.

Workup

  1. filtrationThe product was filtered off under suction
  2. customrecrystallized from dimethylformamide/water
  3. custom1/4H2O were obtained as colorless crystals of melting point 238°-240° C.

Sources & evidence

ORD record
ord-1e616fb0db5a48fdb197eb6c4437ee72
Source dataset
uspto-grants-1987_01
Patent number
US04636504

Reaction notes

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