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

HRID 1444560Notes

Reaction equation

HRID 1444560 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-ff2a996d2b714151a6edb9343f3170a8
Source dataset
uspto-grants-2010_02
Patent number
US07662849B2

Reaction notes

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