Hydrochloric Acid → Ethyl 2-methyl-2-(piperidin-4-YL)propanoate

HRID 977161Notes

Reaction equation

HRID 977161 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:22])[C:6]([CH3:21])([CH3:20])[C:7]1[CH2:8][CH2:9][N:10](CC2C=CC=CC=2)[CH2:11][CH:12]=1)[CH3:3].[H][H].[OH-].[Na+]>C(O)C.O.[Pd]>[CH2:2]([O:4][C:5](=[O:22])[C:6]([CH3:21])([CH3:20])[CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 545483681-Phenylmethyl-alpha,alpha-dimethyl-1,2,3,6-tetrahydro-4-pyridine-acetic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 49759624Ethyl 2-methyl-2-(piperidin-4-YL)propanoateYield 82%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 246 g (76.6×10-2 mole) of the hydrochloride of 1-phenylmethyl-α,α-dimethyl-1,2,3,6-tetrahydro-4-pyridine-acetic acid ethyl ester in 1.5 liters of ethanol was hydrogenated in a Parr's apparatus at 50° C. at a hydrogen pressure of 3.106Pa in the presence of 20 g of 5% palladium/charcoal. After filtering, the filtrate obtained was evaporated off under reduced pressure. The residue obtained was taken up in water and rendered alkaline with 500 ml of 5N sodium hydroxide. It was extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and filtered and the solvents were evaporated off under reduced pressure. 125.3 g (yield: 82%) of the desired product was obtained as an oil. n21 =1.47

Workup

  1. filtrationAfter filtering
  2. customthe filtrate obtained
  3. customwas evaporated off under reduced pressure
  4. customThe residue obtained
  5. extractionIt was extracted with ethyl acetate
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvents were evaporated off under reduced pressure

Sources & evidence

ORD record
ord-073a01532a0944e0b1b5c8cc5092b470
Source dataset
uspto-grants-1997_03
Patent number
US05614534

Reaction notes

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