p-Toluenesulfonic acid → Methyl 4-amino-3-methylpiperidine-1-carboxylate

HRID 1729797Notes

Reaction equation

HRID 1729797 reaction equation
[CH3:1][CH:2]1[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][CH3:12])=[O:10])[CH2:3]1.C1(C[NH2:20])C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1.[H][H]>[Pd].CO>[NH2:20][CH:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH:2]1[CH3:1]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7504BenzylamineHCID 3015586Methyl 3-methyl-4-oxopiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 19785295Methyl 4-amino-3-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred mixture of 85.6 parts of methyl 3-methyl-4-oxo-1-piperidinecarboxylate and 240 parts of methanol are added 54.6 parts of benzenemethanamine (exothermic reaction). After stirring for 5 minutes, there are added 0.2 parts of 4-methylbenzenesulfonic acid and the whole is hydrogenated at normal pressure and at normal temperature with 10 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, (about 20 hours), the catalyst is filtered off and the filtrate is evaporated. The residue is distilled, yielding methyl 4-amino-3-methyl-1-piperidinecarboxylate; bp. 136°-140° C. (water-jet).

Workup

  1. custom, (about 20 hours),
  2. filtrationis filtered off
  3. customthe filtrate is evaporated
  4. distillationThe residue is distilled

Sources & evidence

ORD record
ord-e557ef56625e4b778c5fb79708deba4d
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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