Toluene → 2,6-Dimethyl-4-(2-methyl-3-(4-(2-methylbutan-2-yl)phenyl)propyl)morpholine

HRID 1395206Notes

Reaction equation

HRID 1395206 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:16])[CH:14]=O)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[CH3:17][CH:18]1[O:23][CH:22]([CH3:24])[CH2:21][NH:20][CH2:19]1.C1(C)C=CC=CC=1.[H][H]>[Pd].O>[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:16])[CH2:14][N:20]2[CH2:19][CH:18]([CH3:17])[O:23][CH:22]([CH3:24])[CH2:21]2)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 1108622,6-DimethylmorpholineHCID 2289892-Methyl-3-[4-(2-methylbutan-2-yl)phenyl]propanalHCID 178418361HCID 178418361, compound

Product 1

HCID 21682,6-Dimethyl-4-(2-methyl-3-(4-(2-methylbutan-2-yl)phenyl)propyl)morpholine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Procedure

230 G. of 3-(p-tert.-amyl-phenyl)-2-methyl-propionaldehyde and 137 g. of 2,6-dimethylmorpholine are heated at reflux in 1000 ml. of toluene for 16 hours in a water-separator under nitrogen gasification until the water-cleavage has been completed. 17.5 G. of 5% palladium/carbon are added at room temperature under nitrogen gasification and the mixture is subsequently hydrogenated until the hydrogen uptake has been completed. Then, the catalyst is removed by filtration and the toluene is evaporated in vacuo. By distillation of the residue, there is obtained pure 4-[3-(p-tert.-amyl-phenyl)-2-methyl-propyl]-2,6-dimethylmorpholine having a boiling point of 134° C./0.036 Torr.

Workup

  1. temperatureat reflux in 1000 ml
  2. customThen, the catalyst is removed by filtration
  3. customthe toluene is evaporated in vacuo
  4. distillationBy distillation of the residue

Sources & evidence

ORD record
ord-a0b36f42397247ba97b4ebc3cae3f7cc
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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