Benzyl Chloride → N,N-dibenzyl-N'-diphenylmethyl-ethylenediamine

HRID 544130Notes

Reaction equation

HRID 544130 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:16][CH2:17][CH2:18][NH2:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[CH2:1]([N:19]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:18][CH2:17][NH:16][CH:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 11031568(2-Aminoethyl)(diphenylmethyl)amine

Product 1

HCID 20459488N,N-dibenzyl-N'-diphenylmethyl-ethylenediamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2.9 g of benzyl chloride in 25 ml of acetonitrile is added to 5.6 g of N-diphenylmethyl-ethylenediamine in 30 ml of boiling acetonitrile. The mixture is heated under reflux for 12 hours, concentrated and partitioned between diethyl ether and 10% sodium hydroxide solution. The organic phases are dried over sodium sulphate and concentrated by evaporation. The residue can be recrystallised from methanol or diisopropyl ether. N,N-dibenzyl-N'-diphenylmethyl-ethylenediamine having a melting point of 89°-91° C. is obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. concentrationconcentrated
  4. custompartitioned between diethyl ether and 10% sodium hydroxide solution
  5. dry with materialThe organic phases are dried over sodium sulphate
  6. concentrationconcentrated by evaporation
  7. customThe residue can be recrystallised from methanol or diisopropyl ether

Sources & evidence

ORD record
ord-f13cc3b3638f4770895ed12a07fcb520
Source dataset
uspto-grants-1984_05
Patent number
US04448776

Reaction notes

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