Water → HCID 19707180, compound

HRID 726581Notes

Reaction equation

HRID 726581 reaction equation
[O:1]([C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]2)=[N:15][CH:16]=1)=O)C1C=CC=CC=1.O.[NH2:29][NH2:30].O>O1CCOCC1>[NH:29]([C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]2)=[N:15][CH:16]=1)=[O:1])[NH2:30]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 19707186HCID 19707186, compound

Product 1

HCID 19707180HCID 19707180, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 4-[5-[(phenoxycarbonyl)amino]-2-pyridinyl]-1-piperazinecarboxylate (0.3 mol crude residue) and hydrazine hydrate (1.5 mol) in 1,4-dioxane (1100 ml) was stirred for 6 hours at room temperature. The reaction mixture was poured into water (4000 ml) and the resulting precipitate was filtered. The filtrate was extracted three times with CH2Cl2 (700 ml each time). The separated organic layer was washed with water, dried, filtered and the solvent was evaporated. The residue was stirred in DIPE. The precipitate was filtered and dried (25° C.; 20 hours), yielding 62 g (67%) of ethyl 4-[5-[(hydrazinocarbonyl)amino]-2-pyridinyl]-1-piperazinecarboxylate (interm. 9).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. extractionThe filtrate was extracted three times with CH2Cl2 (700 ml each time)
  3. washThe separated organic layer was washed with water
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. stirringThe residue was stirred in DIPE
  8. filtrationThe precipitate was filtered
  9. customdried (25° C.; 20 hours)

Sources & evidence

ORD record
ord-91d8cf1c000c439682227b992867306d
Source dataset
uspto-grants-1998_01
Patent number
US05710156

Reaction notes

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