Hydrazine → 2-(4-acetylpiperazinyl)-N-aminoacetamide

HRID 2183275Notes

Reaction equation

HRID 2183275 reaction equation
Br[CH2:2][C:3]([O:5]C)=O.[C:7]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+].[NH2:22][NH2:23]>C(O)C>[C:7]([N:10]1[CH2:15][CH2:14][N:13]([CH2:2][C:3]([NH:22][NH2:23])=[O:5])[CH2:12][CH2:11]1)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 9321HydrazineHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate2×HCID 837951-Acetylpiperazine

Product 1

HCID 224797542-(4-acetylpiperazinyl)-N-aminoacetamideYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

The procedure described for Example 283 A was followed using methyl bromoacetate (1.5 g, 0.01 mol), 1-acetyl piperazine (1.4 g, 0.011 mol), and potassium carbonate (1.52 g, 0.011 mol). After one day, an additional 0.3 equivalent of methyl bromoacetate was added to the reaction. The crude material was taken up in approximately 152 mL of ethanol and hydrazine was added to the solution (0.25 mL, 0.008 mol). This was heated in a sealed tube at 85° C. for 4 hours. The solvent was removed to yield the title compound (1.6 g, 80% yield). 1H NMR (DMSO-d6) δ 9.0 (s, 1H), 4.2 (br s, 2H), 3.5 (m, 4H), 2.9 (s, 2H), 2.4 (m, 4H), 2.0 (s, 3H).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-317044e807ea4fada5507255564471a3
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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