Ethylamine → Ethyl-(3,5,5-trimethyl-cyclohex-2-enylidene)-amine

HRID 1250431

Reaction equation

HRID 1250431 reaction equation
[CH2:1]([NH2:3])[CH3:2].O=[C:5]1[CH2:12][C:9]([CH3:11])([CH3:10])[CH2:8][C:7]([CH3:13])=[CH:6]1.[OH-].[K+]>O.Cl.C(N)C>[CH2:1]([N:3]=[C:5]1[CH2:12][C:9]([CH3:11])([CH3:10])[CH2:8][C:7]([CH3:13])=[CH:6]1)[CH3:2]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 6544IsophoroneHCID 14797Potassium Hydroxide

Product 1

HCID 11205971Ethyl-(3,5,5-trimethyl-cyclohex-2-enylidene)-amineYield 95%

Reagents, catalysts & solvents 2

HCID 11198Ethylamine hydrochlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

Ethylamine (42 ml of a 70% solution in water, 530 mmol) is added slowly to a stirred mixture of isophorone (9.67 g, 70 mmol) and ethylamine hydrochloride (0.29 g, 3.5 mmol) at -7° C. After the addition is complete, the temperature of the mixture is allowed to rise to room temperature, and the mixture is stirred for a further 72 hours. The mixture is subsequently cooled to 10° C., and potassium hydroxide (44.9 g, 800 mmol) is added in portions. After 45 minutes, ice is added and the mixture is stirred. The organic phase is then separated, dried over sodium sulfate and evaporated in vacuo to give the crude product (11.0 g, 95%) as a yellow oil, which is used immediately without further purification in the following step.

Workup

  1. additionAfter the addition
  2. customto rise to room temperature
  3. waitAfter 45 minutes
  4. additionice is added
  5. stirringthe mixture is stirred
  6. customThe organic phase is then separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-8887aaeb7acf41b3b6651a248c950fa4
Source dataset
uspto-grants-2002_01
Patent number
US06339042B1

Linked notes

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