Chloroacetonitrile → (4-methylpiperazin-1-yl)acetonitrile

HRID 2214529Notes

Reaction equation

HRID 2214529 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:15][C:16]#[N:17]>C(#N)C.C(OCC)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:15][C:16]#[N:17])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 10582860(4-methylpiperazin-1-yl)acetonitrileYield 77.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-methyl piperazine (0.55 mL, 5.0 mmol), potassium carbonate (3.49 g, 25 mmol) and chloroacetonitrile (0.34 mL, 5.6 mmol) in acetonitrile (3 mL) was stirred at room temperature 8 h. The mixture was diluted with diethyl ether and filtered and concentrated to yield the title compound as yellow crystals (536.6 mg, 77% yield). 1H NMR (500 MHz, CDCl3) δ: 3.50 (s, 2H), 2.66 (t, 4H, J=4.58), 2.52 (bs, 4H), 2.33 (s, 3H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-bee3b020bd83476a82f1973a2f993065
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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