Hydrochloric Acid → HCID 57880459, compound

HRID 643539Notes

Reaction equation

HRID 643539 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C@H:10]([CH3:25])[CH2:9]1)C1C=CC=CC=1.Cl>CCO.[Pd]>[CH3:25][C@H:10]1[C@H:11]([C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57880504HCID 57880504, compound

Product 1

HCID 57880459HCID 57880459, compoundYield 109%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-[(3S,4R)-1-benzyl-3-methylpiperidin-4-yl]benzoate (9 g, 26.7 mmol) was dissolved in EtOH:1M HCl (1:1, 160 mL) and was hydrogenated at 50 psi in the presence of a catalytic amount of palladium on carbon (1 g) for 36 hr. Palladium was filtered through a celite plug and the filtrate was evaporated to dryness to give 7.2 g of ethyl 3-[(3S,4R)-3-methylpiperidin-4-yl]benzoate as an HCl salt.

Workup

  1. filtrationPalladium was filtered through a celite plug
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-eec81e3c5c294774b6b14f0bd5292ecb
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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