Methoxyisopropylamine → HCID 20543892, compound

HRID 2397512Notes

Reaction equation

HRID 2397512 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH3:9])[C:4]1=O)[CH3:2].[CH3:11][CH:12]([NH2:16])[CH2:13][O:14][CH3:15]>C1(C)C=CC=CC=1.CCOCC.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH3:9])[C:4]1=[N:16][CH:12]([CH3:11])[CH2:13][O:14][CH3:15])[CH3:2]

Participants

6

Reactant 2

HCID 123458MethoxyisopropylamineHCID 20269722HCID 20269722, compound

Product 1

HCID 20543892HCID 20543892, compoundYield 50.2%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

163 g of titanium tetrachloride in 800 ml of toluene were added dropwise to a solution of 229 g (1.64 mole) of 2-ethyl-6-methylcyclohexanon and 435 g (4.9 mole) of 1-methyl-2-methoxyethylamine in 1000 ml toluene and 110 ml of ether over a period of two hours with stirring and at a temperature of between 0°-10° C. After distilling off the ether the reaction mixture was refluxed for 61/2 hours. After cooling the precipitate was filtered off and the filtrate concentrated in a rotary evaporator at 50° C. Distillation of the residue under reduced pressure gave 174 g 2-ethyl-6-methyl-N-(1-methyl-2-methoxyethyl)-cyclohexylidene-amine, m.p. 109°-113° C./15 Torr.

Workup

  1. distillationAfter distilling off the ether the reaction mixture
  2. temperaturewas refluxed for 61/2 hours
  3. temperatureAfter cooling the precipitate
  4. filtrationwas filtered off
  5. concentrationthe filtrate concentrated in a rotary evaporator at 50° C
  6. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-e4ac39a852ff4edc8b60ac5c128e7302
Source dataset
uspto-grants-1977_05
Patent number
US04022611

Reaction notes

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