Water → HCID 487663, compound

HRID 1733264Notes

Reaction equation

HRID 1733264 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:15])[CH:13]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][CH:17]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]1.O.[H][H]>C1(C)C=CC=CC=1.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:15])[CH2:13][N:19]2[CH2:20][CH2:21][CH2:22][CH:17]([CH3:16])[CH2:18]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962Water2×HCID 790813-MethylpiperidineHCID 228987LilialHCID 178418361HCID 178418361, compound

Product 1

HCID 487663HCID 487663, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

4.45 Kg. of 3-(p-tert.-butyl-phenyl)-2-methyl-propionaldehyde and 2.38 kg. of 3-methyl-piperidine are heated at reflux in 3.42 liters of toluene for 16 hours in a water-separator under nitrogen gasification until the water-cleavage has been completed. 197 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. The catalyst is then removed by filtration and the toluene evaporated in vacuo. By distillation of the residue, there is obtained pure 1-[3-(p-tert.-butyl-phenyl)-2-methyl-propyl]-3-methyl-piperidine, having a boiling point of 115°-117° C./0.02 Torr.

Workup

  1. customThe catalyst is then removed by filtration
  2. customthe toluene evaporated in vacuo
  3. distillationBy distillation of the residue

Sources & evidence

ORD record
ord-22ffee5094644dfaadcb041dc4a76b60
Source dataset
uspto-grants-1980_12
Patent number
US04241058

Reaction notes

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