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Acetic Acid → 1-Ethyl-4,4'-bipiperidine

HRID 1699260
Notes
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Reaction equation

HRID 1699260 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][N:12](C(OCC3C=CC=CC=3)=O)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)[CH3:2].O.C(O)(=O)C.[H][H]>CO.[Pd]>[CH2:1]([N:3]1[CH2:4][CH2:5][CH:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:7][CH2:8]1)[CH3:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 183212841-Ethyl-4-[1-(phenylmethoxycarbonyl)-4-piperidinyl]piperidineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 183210271-Ethyl-4,4'-bipiperidine

Reagents, catalysts & solvents 2

HCID 23938Palladium
On this pageParticipantsProcedureSources & evidenceReaction notes
Catalyst
HCID 887MethanolSolvent

Procedure

A solution of 7.6 g (0.023 mol) of 1-ethyl-4-[1-(phenylmethoxycarbonyl)-4-piperidinyl]piperidine in a mixture of 70 ml of methanol, 30 ml of water and 10 ml of glacial acetic acid was hydrogenated in the presence of 10% palladium/charcoal at room temperature and 3 bar of hydrogen pressure until the uptake of hydrogen had ceased. After working up in the usual way the desired compound was obtained as a colourless oil in a quantitative yield.

Sources & evidence

ORD record
ord-3a221bd33f7b4f9fba11f8c3e3113b9d
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06344449B1

Reaction notes

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