Acetic Acid → Piperidine, acetate

HRID 1833786Notes

Reaction equation

HRID 1833786 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H].[C:9]([OH:12])(=[O:11])[CH3:10]>C(O)C.[Pd]>[C:9]([OH:12])(=[O:11])[CH3:10].[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8082PiperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 9793820Piperidine, acetateYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 1.0 gram amount of 4-ethyl-1[NG,NG -dibenzyloxycarbonyl-N2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginyl]piperidine was dissolved in a mixture of 50 ml of ethanol and 5 ml of acetic acid. An 0.5 gram amount of palladium-black was added to the mixture, which was then shaken in a stream of hydrogen for 10 hours at room temperature. After filtering off the catalyst, the filtrate was evaporated to give a viscous oily product. Reprecipitation from ethanolethyl ether gave 4-ethyl-1[N2 -7-methoxy-2-naphthalenesulfonyl)-L-arginyl]piperidine acetate in a powder form in 76% yield.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customthe filtrate was evaporated
  3. customto give a viscous oily product
  4. customReprecipitation from ethanolethyl ether

Sources & evidence

ORD record
ord-362f728c42bd4c9ca6fa3ae4b148bc64
Source dataset
uspto-grants-1978_01
Patent number
US04066758

Reaction notes

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