Hydrochloric Acid → HCID 10565521, compound

HRID 865932Notes

Reaction equation

HRID 865932 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH:20]([CH3:22])[CH3:21])(O)[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].Cl.[H][H]>[Pd].CO>[C:1]([N:6]1[CH2:7][CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH:20]([CH3:21])[CH3:22])[CH2:10][CH2:11]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 105188151-Carbethoxy-4-[2-(1-methylethoxy)phenyl]-4-piperidinolHCID 178418361HCID 178418361, compound

Product 1

HCID 10565521HCID 10565521, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A crude solution of XV (36 g), 10% palladium on carbon (1.80 g), 5 mL of concentrated HCl and 125 mL of MeOH was shaken on a Parr apparatus under 55.5 psig of hydrogen at 22° C. for 3 d. The reaction was filtered over Celite, and concentrated to a residue. This material was partitioned between ether and water. The organic solution was dried (MgSO4), filtered, and concentrated to yield 29.34 g of XVI as a light yellow oil which was carried forward without further purification. The structure was supported by MS and 1H NMR.

Workup

  1. filtrationThe reaction was filtered over Celite
  2. concentrationconcentrated to a residue
  3. customThis material was partitioned between ether and water
  4. dry with materialThe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cebf284b129c484aa90ff48f4425981c
Source dataset
uspto-grants-1996_10
Patent number
US05569659

Reaction notes

Loading…