Piperidine → Fenpropidin

HRID 894379

Reaction equation

HRID 894379 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:15])[CH2:13]O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>[Pd].CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:15])[CH2:13][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 92013Benzenepropanol, 4-(1,1-dimethylethyl)-beta-methyl-

Product 1

HCID 91694FenpropidinYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 153 parts of 3-p-tertiary butylphenyl-2-methyl-propanol, 70 parts of piperidine, 230 parts of methanol and 20 parts of catalyst, comprising 0.5% by weight of Pd and 5% by weight of Nd2O3 on Al2O3, is hydrogenated in a stirred autoclave of 1,000 parts by volume capacity, at 70° C. under a hydrogen pressure of 50 bar, until the pressure remains constant. The autoclave is then allowed to cool, the catalyst is filtered off and the filtrate is purified by distillation. 195 parts of N-(3'-(p-tertiary butylphenyl)-2'-methylpropyl)-piperidine, boiling point 117° C./0.2 mm Hg, are obtained. The yield is 94% of theory.

Workup

  1. customis hydrogenated in a stirred autoclave of 1,000 parts by volume capacity, at 70° C. under a hydrogen
  2. temperatureto cool
  3. filtrationthe catalyst is filtered off
  4. distillationthe filtrate is purified by distillation

Sources & evidence

ORD record
ord-6cac709ee57a40e2a5318f5e20149460
Source dataset
uspto-grants-1981_08
Patent number
US04283534

Linked notes

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