Allylamine → Allyl-(2,2-dimethyl-pent-4-enylidene)-amine

HRID 751461Notes

Reaction equation

HRID 751461 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:5][CH:6]=[CH2:7])[CH:3]=O.[CH2:9]([NH2:12])[CH:10]=[CH2:11]>C1C=CC=CC=1>[CH2:9]([N:12]=[CH:3][C:2]([CH3:1])([CH3:8])[CH2:5][CH:6]=[CH2:7])[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 796362,2-Dimethylpent-4-enal

Product 1

HCID 22928390Allyl-(2,2-dimethyl-pent-4-enylidene)-amineYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,2-Dimethyl-4-pentenal (2.8 g, 25 mmol) was dissolved in 15 mL benzene. To this solution allylamine (2.85 g, 50 mmol) was added. A few molecular sieves were used to absorb water generated during the reaction. The mixture was stirred at room temperature overnight. Removal of the solvent and excess amount of allylamine on rotavapor provided 3.76 g of the title compound as clear liquid (yield 100%). 1H-NMR (400 MHz, CDCl3): •7.52(s, 1H), 5.99-5.90(m, 1H), 5.80-5.70(m, 1H), 5.15-4.99(m, 4H), 4.01-3.99(m, 2H), 2.17(d, 2H), 1.06(s, 6H).

Workup

  1. customto absorb water
  2. customgenerated during the reaction
  3. customRemoval of the solvent and excess amount of allylamine on rotavapor

Sources & evidence

ORD record
ord-f24895c55c78484da8f31d9a87f89b0d
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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