Hydrazine hydrate (1:1) → 4-(2-[4-(4-Methoxyphenyl)piperazin-1-yl]pyridin-5-yl)semicarbazide

HRID 1493594Notes

Reaction equation

HRID 1493594 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](OC4C=CC=CC=4)=[O:23])=[CH:17][N:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.O.[NH2:32][NH2:33]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:23])[NH:32][NH2:33])=[CH:17][N:16]=3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 149868892-(4-[4-Methoxyphenyl]piperazin-1-yl)-5-phenoxycarbonylaminopyridine

Product 1

HCID 149868904-(2-[4-(4-Methoxyphenyl)piperazin-1-yl]pyridin-5-yl)semicarbazide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product of part (iii) (2.8 g, 6.9 mmole) and hydrazine hydrate (7.5 ml, 150 mmole) in 1,4-dioxane (50 ml) was heated under reflux for 1.5 hours. The cooled mixture was filtered to provide a solid which was washed with ether to yield the desired product, m.p. 280°-282° (2.0 g, 85%), which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. filtrationThe cooled mixture was filtered
  4. customto provide a solid which
  5. washwas washed with ether

Sources & evidence

ORD record
ord-2dca8184035f4449bfeaa7aca13d02cb
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

Loading…