Hydrochloric Acid → Methyl piperidin-2-ylacetate

HRID 1457721Notes

Reaction equation

HRID 1457721 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[CH3:12]O.Cl.[H][H]>C(O)(=O)C.[Pt](=O)=O>[CH3:12][O:10][C:9](=[O:11])[CH2:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][NH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 178418361HCID 178418361, compound

Product 1

HCID 5214606Methyl piperidin-2-ylacetateYield 75.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Pyridylacetic acid hydrochloride (10.00 g, 57.6 mmol) and platinum(IV) oxide (1.00 g, 4.4 mmol) were shaken in a mixture of 75 ml acetic acid, 75 ml methanol, and 10 ml conc. HCl on Parr under 60 psi hydrogen at room temperature overnight. The mixture was then filtered through Celite, and the filtrate evaporated under reduced pressure to yield 8.42 g (75.9%) of the title compound as an off-white solid. MS (NH3 -CI/DDIP): m/e 158 (M+H)+. 1H NMR (300 MHz, CDCl3): δ 1.50-1.96 (m, 6H); 2.80 (m, 2H); 3.20-3.60 (m, 3H); 3.76 (s, 3H). 13C NMR (60 MHz, d6 -DMSO): δ 21.94; 28.05; 37.46; 40.49; 44.12; 57.33; 52.74; 170.39.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-0142ff3a602c42b6817211eaab7d522e
Source dataset
uspto-grants-1998_12
Patent number
US05849736

Reaction notes

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