HCID 12432684, compound → HCID 13733716, compound

HRID 620711Notes

Reaction equation

HRID 620711 reaction equation
[C:1]1([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:2]([CH3:8])=[CH:3][CH:4]=[CH:5][C:6]=1[CH3:7].[H][H]>C(O)(=O)C.O=[Pt]=O>[C:1]1([O:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][NH:12]2)[C:2]([CH3:8])=[CH:3][CH:4]=[CH:5][C:6]=1[CH3:7]

Participants

5

Reactant 2

HCID 12432684HCID 12432684, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13733716HCID 13733716, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Twenty-nine (29) g of 2-[(2,6-xyloxy)methyl]pyridine were hydrogenated in 250 mls of concentrated acetic acid using hydrogen in the presence of 1.0 g of PtO2. The hydrogenation took place by introducing hydrogen to theoretical volume at 70°-80° C. in an autoclave at a pressure of 5-10 atmospheres. The catalyst was filtered off, and the acetic acid evaporated. Twenty-four (24) g of 2-[(2,6-xyloxy)methyl]piperidine were obtained. The acetic acid salt produced was dissolved in 300 mls of water and was purified with active carbon, whereupon the product was precipitated as the base using ammonia. The base product was dried and dissolved in 150 mls of methyl ethyl ketone, whereupon the hydrochloride was obtained by neutralizing with dry HCl. The hydrochloride of 2-[(2,6-xylyoxy)methyl]piperidine melted at 227°-229° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe acetic acid evaporated

Sources & evidence

ORD record
ord-48ceb7953e0441d79d8851e6a9084aef
Source dataset
uspto-grants-1989_04
Patent number
US04822778

Reaction notes

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