Hydrazine hydrate (1:1) → N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamide

HRID 1154746

Reaction equation

HRID 1154746 reaction equation
C1(O[C:8](=[O:30])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)C=CC=CC=1.O.[NH2:32][NH2:33]>O1CCOCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([N:19]2[CH2:18][CH2:17][N:16]([C:13]3[CH:12]=[CH:11][C:10]([NH:9][C:8]([NH:32][NH2:33])=[O:30])=[CH:15][CH:14]=3)[CH2:21][CH2:20]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 981607Phenyl N-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate

Product 1

HCID 820816N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamideYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3.2 parts of phenyl{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}carbamate, 50 parts of hydrazine hydrate and 100 parts of 1,4-dioxane is stirred and refluxed for 3 hours. The reaction mixture is cooled and poured onto water. The precipitated product is filtered off and crystallized from N,N-dimethylformamide, yielding 1.7 parts (63%) of N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamide; mp. +300° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. filtrationThe precipitated product is filtered off
  5. customcrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-4aa61dbe063646409146570b46a0809d
Source dataset
uspto-grants-1984_12
Patent number
US04490530

Linked notes

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