Hydrochloric Acid → HCID 9952466, compound

HRID 1872753Notes

Reaction equation

HRID 1872753 reaction equation
C([O:8][N:9]([C@@H:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[C:10](=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)C1C=CC=CC=1.Cl.[NH4+].[OH-]>[Pd].CO>[Cl:19][C:14]1[CH:13]=[C:12]([CH2:11][C:10]([N:9]([OH:8])[C@@H:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:20])[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 54345572HCID 54345572, compound

Product 1

HCID 9952466HCID 9952466, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension mixture of N-benzyloxy-2-(3,4-dichlorophenyl)-N-[1-(S)-phenyl-2-(1-pyrrolidinyl)ethyl]acetamide (1.60 g, 3.3 mmol), 10% palladium on carbon (0.16 g), and HCl gas saturated methanol (20 ml) in methanol (20 ml) was stirred under hydrogen atmosphere at room temperature for 13 h. After removal of the catalyst by Celite filtration, the filtrate was concentrated to give 1.63 g of violet colored viscous oil, which was basified with NH4OH and extracted with CH2Cl2 (20 ml×3). The extract combined was dried (Na2SO4) and concentrated to afford a brown colored crystalline, which was collected by filtration and washed with ether/hexane to give 1.04 g (80%) of pale yellow powder, mp 118-120° C.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby Celite filtration
  3. concentrationthe filtrate was concentrated
  4. customto give 1.63 g
  5. extractionextracted with CH2Cl2 (20 ml×3)
  6. dry with materialThe extract combined was dried (Na2SO4)
  7. concentrationconcentrated
  8. customto afford a brown colored crystalline, which
  9. filtrationwas collected by filtration
  10. washwashed with ether/hexane

Sources & evidence

ORD record
ord-67fb77bebe884900b866967dea137ac1
Source dataset
uspto-grants-2000_08
Patent number
US06110947

Reaction notes

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