Hydrochloric Acid → Fenpropidin

HRID 1733267Notes

Reaction equation

HRID 1733267 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([CH3:20])[CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:20])[CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 571057691-[3-(p-Tert.butyl-phenyl)-2-methyl-2-propenyl]-piperidine

Product 1

HCID 91694Fenpropidin

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 4.5 g of 1-[3-(p-tert.butyl-phenyl)-2-methyl-2-propenyl]-piperidine in 125 ml of alcohol are added 1.7 ml of 32% hydrochloric acid and subsequently 1.5 g of 5% palladium/carbon and the mixture is then hydrogenated. After completion of the hydrogen uptake, the catalyst is filtered, the filtrate is treated with 200 ml of 10% sodium hydroxide and extracted with ether. The combined ether extracts are washed neutral with water, dried and evaporated. By distillation there is obtained pure 1-[3-(p-tert.butyl-phenyl)-2-methyl-propyl]-piperidine of boiling point 104° C./0.032 Torr.

Workup

  1. filtrationAfter completion of the hydrogen uptake, the catalyst is filtered
  2. additionthe filtrate is treated with 200 ml of 10% sodium hydroxide
  3. extractionextracted with ether
  4. washThe combined ether extracts are washed neutral with water
  5. customdried
  6. customevaporated
  7. distillationBy distillation there

Sources & evidence

ORD record
ord-d2245804b7884932bb7f0ff9c2ee880e
Source dataset
uspto-grants-1980_12
Patent number
US04241058

Reaction notes

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