Diethyl Ether → 1-Cyano-3,5,5-trimethylhexylamine

HRID 2212217Notes

Reaction equation

HRID 2212217 reaction equation
[CH3:1][CH:2]([CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3]C=O.[Cl-].[NH4+:12].[CH2:13](OCC)C.[C-:18]#[N:19].[Na+]>O>[C:13]([CH:18]([NH2:19])[CH2:1][CH:2]([CH3:3])[CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])#[N:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 215743,5,5-TrimethylhexanalHCID 25517Ammonium Chloride

Product 1

HCID 574282011-Cyano-3,5,5-trimethylhexylamineYield 34.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of the 3,5,5-trimethylhexanal (17.4 mL, 0.10 mol), ammonium chloride (53.5 g, 0.205 mol) and diethyl ether (113 mL) was added sodium cyanide (7.35 g, 0.15 mol) in water (38 mL). The reaction mixture was allowed to stir vigorously for 16 h. The layers were separated. The aqueous layer was extracted with diethyl ether. The combined organic layer was then extracted with 1 N HCl. Saturated sodium bicarbonate was then added until 1-cyano-3,5,5-trimethyl-hexylamine was completely precipitated. Vacuum filtration and washing with 5 mL ice cold water followed by lyophilization gave 1-cyano-3,5,5-trimethylhexylamine (5.805 g, 0.034 mol, 34.5%) as a white solid.

Workup

  1. customThe layers were separated
  2. extractionThe aqueous layer was extracted with diethyl ether
  3. extractionThe combined organic layer was then extracted with 1 N HCl
  4. additionSaturated sodium bicarbonate was then added until 1-cyano-3,5,5-trimethyl-hexylamine
  5. customwas completely precipitated
  6. filtrationVacuum filtration
  7. washwashing with 5 mL ice cold water

Sources & evidence

ORD record
ord-4e1f8fc0ecd14255b61ed9edd128a671
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

Loading…