Ethylenediamine → N-(4-chlorobenzyl)ethane-1,2-diamine

HRID 1154378Notes

Reaction equation

HRID 1154378 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[CH2:10]([NH2:13])[CH2:11][NH2:12].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:12][CH2:11][CH2:10][NH2:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium Hydroxide

Product 1

HCID 13785698N-(4-chlorobenzyl)ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Chlorobenzyl chloride, 32 g. (0.2 mole), was added dropwise to 60 g. (1.0 mole) of ethylenediamine heated at 80°. The solution was stirred at 80° overnight and then the excess amine was distilled in vacuo. The residue was triturated with i-PrOH to yield 32 g. of crude product. This material was dissolved in water, basified with dilute NaOH and the solution extracted with CH2Cl2. The combined extracts were dried (K2CO3) and concentrated in vacuo to an oil. The latter was distilled and the material boiling at 93°-95°/0.06 mm Hg was collected to yield 14.5 g. of the desired product, the identity of which was confirmed by examination of the NMR spectrum.

Workup

  1. addition(0.2 mole), was added dropwise to 60 g
  2. distillationthe excess amine was distilled in vacuo
  3. customThe residue was triturated with i-PrOH
  4. customto yield 32 g
  5. extractionthe solution extracted with CH2Cl2
  6. dry with materialThe combined extracts were dried (K2CO3)
  7. concentrationconcentrated in vacuo to an oil
  8. distillationThe latter was distilled
  9. customthe material boiling at 93°-95°/0.06 mm Hg was collected
  10. customto yield 14.5 g

Sources & evidence

ORD record
ord-5c20cf07e184470badb5ec0ae2e375e5
Source dataset
uspto-grants-1984_12
Patent number
US04489078

Reaction notes

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