Triethylamine → 2-Cyano-1,4-dihydro-1-dimethylamino-5-ethylpyridine

HRID 1650341Notes

Reaction equation

HRID 1650341 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5](NC)=[CH2:6].Cl[C:11](=[CH2:14])[C:12]#[N:13].[CH2:15]([N:17](CC)[CH2:18]C)C.O1CCOC[CH2:23]1>>[C:12]([C:11]1[N:2]([N:17]([CH3:18])[CH3:15])[CH:3]=[C:4]([CH2:5][CH3:6])[CH2:23][CH:14]=1)#[N:13]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 701982-ChloroacrylonitrileHCID 867439001-Dimethylamino-1-aza-3-ethyl-1,3-butadiene

Product 1

HCID 144186782-Cyano-1,4-dihydro-1-dimethylamino-5-ethylpyridine

Procedure

12.6 g of 1-dimethylamino-1-aza-3-ethyl-1,3-butadiene, 8 ml of 2-chloroacrylonitrile and 27.8 ml of triethylamine are heated in 40 ml of dioxane for 31/2 hours to 70° C. The reaction mixture is concentrated by evaporation and the residue is chromatographed over silica gel with a 16:1 mixture of hexane/ethyl acetate, affording 8.2 g of the title compound as a yellow oil which, on standing at room temperature, spontaneously reacts further to 2-cyano-5-ethylpyridine, with elimination of dimethylamine.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. customthe residue is chromatographed over silica gel with a 16:1 mixture of hexane/ethyl acetate

Sources & evidence

ORD record
ord-ab770a4de3254cf69fe98e7abb82bac6
Source dataset
uspto-grants-1990_05
Patent number
US04923993

Reaction notes

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