Hydrazine hydrate (1:1) → 1-Piperazineacetic acid, 4-methyl-, hydrazide

HRID 34271Notes

Reaction equation

HRID 34271 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([O:11]C)=O)[CH2:4][CH2:3]1.O.[NH2:14][NH2:15]>C(O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]([NH:14][NH2:15])=[O:11])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 6422228Methyl (4-methylpiperazin-1-yl)acetate

Product 1

HCID 905661-Piperazineacetic acid, 4-methyl-, hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-methyl-1-piperazinyl)acetic acid, methyl ester (16.3 g., 0.0946 mole) and hydrazine monohydrate (7.0 ml., 0.142 mole) in ethanol (100 ml.) was refluxed for 17 hours and the solvent was removed under vacuum. The residue was triturated with ether with cooling at -78° and the resulting solid was filtered. The product was triturated again with ether-ethyl acetate to give 2-(4-methyl-1-piperazinyl)acetic acid, hydrazide as a solid melting at 87°-89° C. (8.94 g., 55%).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe residue was triturated with ether
  3. temperaturewith cooling at -78°
  4. filtrationthe resulting solid was filtered
  5. customThe product was triturated again with ether-ethyl acetate

Sources & evidence

ORD record
ord-4a6be609942f4fad937045df88a62eb1
Source dataset
uspto-grants-1988_08
Patent number
US04761415

Reaction notes

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