Perchloric Acid → 1-[3-(4-Tert.-amylcyclohexyl)-2-methyl-propyl]-piperidine

HRID 1395209Notes

Reaction equation

HRID 1395209 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:21])[CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].Cl(O)(=O)(=O)=O>[Pt](=O)=O.C(O)(=O)C>[C:1]([CH:6]1[CH2:7][CH2:8][CH:9]([CH2:12][CH:13]([CH3:21])[CH2:14][N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:10][CH2:11]1)([CH2:4][CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 190989441-[3-(p-Tert.amyl-phenyl)-2-methyl-propyl]-piperidine

Product 1

HCID 203405401-[3-(4-Tert.-amylcyclohexyl)-2-methyl-propyl]-piperidine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent2×

Procedure

7 G. of platinum dioxide and 7 g. of active carbon are suspended in 500 ml. of glacial acetic acid and prehydrogenated. Subsequently, there is added a solution of 37.4 g. of 1-[3-(p-tert.-amyl-phenyl)-2-methyl-propyl]-piperidine in 1000 ml. of glacial acetic acid and 67 ml. of perchloric acid and the mixture is hydrogenated at 25° C. The hydrogenation solution is filtered to remove the catalyst and the filtrate is treated with 110 g. of potassium acetate dissolved in 100 ml. of water. The precipiated potassium perchlorate is removed by filtration and the filtrate is evaporated on a rotary evaporator. The crystalline residue is made alkaline with 2 N sodium hydroxide, the free base is extracted with 500 ml. of ether, washed neutral with water, dried over sodium sulfate and evaporated. By distillation, there is obtained pure 1-[3-(4-tert.-amylcyclohexyl)-2-methyl-propyl]-piperidine, having a boiling point of 128°-132° C./0.04 Torr.

Workup

  1. additionSubsequently, there is added a solution of 37.4 g
  2. customis hydrogenated at 25° C
  3. filtrationThe hydrogenation solution is filtered
  4. customto remove the catalyst
  5. additionthe filtrate is treated with 110 g
  6. dissolutionof potassium acetate dissolved in 100 ml
  7. customThe precipiated potassium perchlorate is removed by filtration
  8. customthe filtrate is evaporated on a rotary evaporator
  9. extractionthe free base is extracted with 500 ml
  10. washof ether, washed neutral with water
  11. dry with materialdried over sodium sulfate
  12. customevaporated
  13. distillationBy distillation

Sources & evidence

ORD record
ord-34dcafb8159d45918cac80ec18732658
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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