N,N'-Dimethylethylenediamine → HCID 18924832, compound

HRID 232588Notes

Reaction equation

HRID 232588 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/NH4OH (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-70d37670b281404d923a435deac11b8e
Source dataset
uspto-grants-1997_01
Patent number
US05591737

Reaction notes

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