Ethylenediamine → N-((6-chloro-3-pyridinyl)methyl)-1,2-ethane-diamine

HRID 1519020Notes

Reaction equation

HRID 1519020 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[CH2:10]([NH2:13])[CH2:11][NH2:12]>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][NH:12][CH2:11][CH2:10][NH2:13])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 10997737N-((6-chloro-3-pyridinyl)methyl)-1,2-ethane-diamineYield 100%

Procedure

Next, 20 mL of ethylenediamine was added to 2.0 g (12.4 mmol) of 2-chloro-5-chloromethylpyridine, and the mixture was stirred overnight. Following reaction completion, the reaction mixture was concentrated under reduced pressure, after which acetonitrile was added and insoluble matter were removed by filtration. The filtrate was concentrated under reduced pressure, giving 2.45 g (yield, 100%) of N-((6-chloropyridin-3-yl)methyl)ethane-1,2-diamine.

Workup

  1. customreaction completion
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionafter which acetonitrile was added
  4. custominsoluble matter were removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-31888c88c40642a39db2535cc3326a76
Source dataset
uspto-grants-2015_07
Patent number
US09073866B2

Reaction notes

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