Hydrazine hydrate (1:1) → 3-[4-(2-Methoxyphenyl)piperazin-1-yl]butanohydrazide

HRID 1514163Notes

Reaction equation

HRID 1514163 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH:15]([CH3:22])[CH2:16][C:17](OCC)=[O:18])[CH2:11][CH2:10]1.O.[NH2:24][NH2:25]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH:15]([CH3:22])[CH2:16][C:17]([NH:24][NH2:25])=[O:18])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59536458Ethyl 3-[4-(2-methoxyphenyl)piperazin-1-yl]butanoate

Product 1

HCID 595364653-[4-(2-Methoxyphenyl)piperazin-1-yl]butanohydrazideYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-[4-(2-methoxyphenyl)piperazin-1-yl]butanoate D11 (2.75 g, 8.97 mmol) and hydrazine monohydrate (2.7 g, 53.85 mmol) in ethanol (40 mL) was refluxed for 48 hrs. The solvent was evaporated under reduced pressure, toluene (50 mL) was added and the solvent was evaporated and the resulting light yellow oil was triturated with 50% AcOEt in hexane (10 mL). The resulting white solid was filtered, washed with hexane and dried to afford 2 g (76%) 3-[4-(2-methoxyphenyl)piperazin-1-yl]butanohydrazide D12.

Workup

  1. customThe solvent was evaporated under reduced pressure, toluene (50 mL)
  2. additionwas added
  3. customthe solvent was evaporated
  4. customthe resulting light yellow oil was triturated with 50% AcOEt in hexane (10 mL)
  5. filtrationThe resulting white solid was filtered
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-d5e04f4cc6a94c1cafbabe4c0da12475
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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