Ethylenediamine → N-(pyrazinylmethyl)ethylenediamine

HRID 22226

Reaction equation

HRID 22226 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[N:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[CH2:11]Cl.[OH-].[Na+]>C(#N)C>[N:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[CH2:11][NH:3][CH2:2][CH2:1][NH2:4]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 170169Pyrazine, 2-(chloromethyl)-

Product 1

HCID 13910894N-(pyrazinylmethyl)ethylenediamineYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethylenediamine (30 g) was dissolved in acetonitrile (200 ml), and pyrazinylmethyl chloride (12.9 g) was added dropwise to this solution at 5° to 10° C. After addition, the mixture was stirred at room temperature for 1 hour. Then, a 50% aqueous solution of sodium hydroxide (8 g) was added, and thereafter, volatile materials were removed at a bath temperature of 60° C. under 5 mmHg. The inorganic salt was then removed by filtration. Thus, N-(pyrazinylmethyl)ethylenediamine (14.1 g) was obtained as a colorless oil.

Workup

  1. additionAfter addition
  2. customvolatile materials were removed at a bath temperature of 60° C. under 5 mmHg
  3. customThe inorganic salt was then removed by filtration

Sources & evidence

ORD record
ord-12754f8fb768446eabece947d4a8ee5e
Source dataset
uspto-grants-1995_06
Patent number
US05428032

Linked notes

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