2-Ethylhexylamine → 1-N-(2-ethylhexyl)-4-dicyanomethylene-2,6-dimethyl-1,4-dihydropyridine

HRID 1431896Notes

Reaction equation

HRID 1431896 reaction equation
[CH3:1][C:2]1O[C:4]([CH3:13])=[CH:5][C:6](=[C:8]([C:11]#[N:12])[C:9]#[N:10])[CH:7]=1.[CH2:14]([CH:16]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:17][NH2:18])[CH3:15]>>[CH2:14]([CH:16]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:17][N:18]1[C:2]([CH3:1])=[CH:7][C:6](=[C:8]([C:11]#[N:12])[C:9]#[N:10])[CH:5]=[C:4]1[CH3:13])[CH3:15]

Participants

3

Reactant 2

HCID 77192-EthylhexylamineHCID 1199154-(Dicyanomethylene)-2,6-dimethyl-4H-pyran

Product 1

HCID 167378231-N-(2-ethylhexyl)-4-dicyanomethylene-2,6-dimethyl-1,4-dihydropyridine

Procedure

A solution of 0.5 g (2.9 mmol) of (2,6-dimethyl-4H-pyran-4-ylidene)malononitril in 7.6 ml (6 g, 46.4 mmol) 2-ethyl-1-hexylamine was refluxed for 1 h under nitrogen. Removal of the excess of ethyl-1-hexylamine at reduced pressure left a solid which was recrystallized from 15 ml EtOAc/MeOH 2/1 yielding 0.45 g (55%) of 1-N-(2-ethylhexyl)-4-dicyanomethylene-2,6-dimethyl-1,4-dihydropyridine.

Workup

  1. customRemoval of the excess of ethyl-1-hexylamine at reduced pressure
  2. waitleft a solid which
  3. customwas recrystallized from 15 ml EtOAc/MeOH 2/1 yielding 0.45 g (55%) of 1-N-(2-ethylhexyl)-4-dicyanomethylene-2,6-dimethyl-1,4-dihydropyridine

Sources & evidence

ORD record
ord-4f1613edb89d4506a46a5ac1c2856aa0
Source dataset
uspto-grants-2009_11
Patent number
US07611696B2

Reaction notes

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