N,N'-Dimethylethylenediamine → HCID 18924832, compound

HRID 1288830Notes

Reaction equation

HRID 1288830 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13]Cl)[CH:8]=1>>[CH3:1][N:2]([CH2:13][C:9]1[CH:8]=[N:7][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][NH:5][CH3:6]

Participants

3

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 183583-(Chloromethyl)pyridine

Product 1

HCID 18924832HCID 18924832, compoundYield 47.3%

Procedure

To 7.50 gm of N,N'-dimethylethylenediamine which has been cooled in an ice-ethanol bath is added portionwise over a 30 minute period 1.40 gm of 3-picolyl chloride. After stirring cold for 1 hour after the addition is completed, the reaction mixture is concentrated in vacuo and the residue partitioned between 50 ml of ether and 10 ml of 5N NaOH solution. The organic layer is separated and the aqueous layer extracted 2 times with 50 ml of ether. The combined organic extracts are dried through sodium sulfate and concentrated in vacuo. Chromatography on 150 gm silica gel using CH2Cl2 /CH3OH/NH4αH (90/10/1) as eluent gives 0.930 g of N,N'-dimethyl-N-(3-pyridylmethyl)ethylenediamine.

Workup

  1. additionafter the addition
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. customthe residue partitioned between 50 ml of ether and 10 ml of 5N NaOH solution
  4. customThe organic layer is separated
  5. extractionthe aqueous layer extracted 2 times with 50 ml of ether
  6. dry with materialThe combined organic extracts are dried through sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6955371286f41508649e6d1c86a78af
Source dataset
uspto-grants-1998_05
Patent number
US05747485

Reaction notes

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