Hydrochloric Acid → HCID 66623318, compound

HRID 415099Notes

Reaction equation

HRID 415099 reaction equation
[NH2:1][C:2]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.C(OCC)(=O)C.[H][H].[ClH:33]>[Pd].CO.O1CCOCC1>[ClH:33].[ClH:33].[NH2:1][C:2]1[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 59349603HCID 59349603, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66623318HCID 66623318, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a Parr hydrogenation bottle was added 7.0 g of tert-butyl 4-(2-amino-3-nitrophenoxy)piperidine-1-carboxylate, 10% palladium on carbon (50% w/w water) (2.0 g, wet), ethyl acetate (100 mL) and MeOH (150 mL). The atmosphere of the vessel was replaced by hydrogen gas. The reaction was shaken on a Parr hydrogenator at 40 psi at room temperature, overnight. The catalyst was filtered through a plug of Celite and the filtrate was concentrated under reduced pressure to give a residue, which was dissolved in methanol, cooled in an ice bath and carefully acidified with 4 N hydrogen chloride in 1,4-dioxane and filtered. The resulting filtrate was concentrated under reduced pressure to give of tert-butyl 4-(2,3-diaminophenoxy)piperidine-1-carboxylate dihydrochloride (6.7 g), and was used directly in the next step without any further purification. MS (EI): 308 (MH+).

Workup

  1. filtrationThe catalyst was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a residue, which
  4. temperaturecooled in an ice bath
  5. filtrationfiltered
  6. concentrationThe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c165367842594196a65edf21f61fff8c
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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