p-Toluenesulfonic acid → HCID 21500269, compound

HRID 1729805Notes

Reaction equation

HRID 1729805 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=O)[CH2:5][CH2:4][N:3]1[C:9]([O:11][CH3:12])=[O:10].C1(C[NH2:20])C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1.[H][H]>[Pd].C(O)C>[NH2:20][CH:6]1[CH2:5][CH2:4][N:3]([C:9]([O:11][CH3:12])=[O:10])[CH:2]([CH3:1])[CH2:7]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7504BenzylamineHCID 21500264Methyl 2-methyl-4-oxo-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 21500269HCID 21500269, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 56 parts of methyl 2-methyl-4-oxo-1-piperidinecarboxylate 35.4 parts of benzenemethanamine, 0.1 parts of 4-methylbenzenesulfonic acid and 240 parts of ethanol is stirred for 15 minutes at room temperature. The whole is hydrogenated at normal pressure and at room temperature with 7 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is distilled, yielding methyl 4-amino-2-methyl-1-piperidine carboxylate; bp. 99°-102° C. at 0.2 mm. pressure.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. distillationThe residue is distilled

Sources & evidence

ORD record
ord-d60e0e53fd3c443f8c71a3d92899a21a
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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