1-Methylpiperazine → 2-Isocyano-1-(4-methylpiperazin-1-yl)ethanone

HRID 1971279Notes

Reaction equation

HRID 1971279 reaction equation
[N+:1]([CH2:3][C:4]([O:6]C)=O)#[C-:2].[CH3:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>>[N+:1]([CH2:3][C:4]([N:12]1[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]1)=[O:6])#[C-:2]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 547815Methyl isocyanoacetate

Product 1

HCID 1819132-Isocyano-1-(4-methylpiperazin-1-yl)ethanoneYield 99%

Procedure

Prepared in accordance with Method B with methyl isocyanoacetate (1.0 g, 10.09 mmol) and N-methylpiperazine (1.37 mL, 15.14 mmol). The reaction mixture was stirred overnight at RT and then concentrated. The residue was dissolved in dichloromethane (50 mL) and evaporated. The residue was coevaporated three times with a mixture of CH2Cl2:cyclohexane=50:50 (3×10 mL). After drying 2-isocyano-1-(4-methyl-piperazin-1-yl)-ethanone VIB 01128 was obtained as yellow solid (1.67 g, 99% yield).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. customevaporated
  4. additionwith a mixture of CH2Cl2
  5. dry with materialAfter drying 2-isocyano-1-(4-methyl-piperazin-1-yl)-ethanone VIB 01128

Sources & evidence

ORD record
ord-cb1925c3ceb2463db316e217ef299eb9
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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