Hydrochloric Acid → HCID 12225560, compound

HRID 863585Notes

Reaction equation

HRID 863585 reaction equation
COC1C=CC=CC=1C[NH:10][C@H:11]1[CH:16]2[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]2)[C@H:12]1[CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:26]1([CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:12]2[C@@H:11]([NH2:10])[CH:16]3[CH2:17][CH2:18][N:13]2[CH2:14][CH2:15]3)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1049432-(Diphenylmethyl)-N-[(2-methoxyphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 12225560HCID 12225560, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(2S,3S)-N-(2-methoxyphenyl)methyl-2-diphenylmethyl-1-azabicyclo[2.2.2]octan-3-amine (4.13 g, 10 mmol) was hydrogenated in methanol (MeOH) (40 ml)/6N HCl (10 ml) by using 20% palladium hydroxide on carbon (0.2 g) at 2.5 kg/cm2 of hydrogen for 60 hours. The filtrate was concentrated and the residue was partitioned between 2N NaOH and CH2Cl2. The organic layer was dried over MgSO4, and concentrated to give the crude product, which was recrystallized from ethanol (EtOH) to afford the pure title compound (2.80 g, 96%).

Workup

  1. customfor 60 hours
  2. concentrationThe filtrate was concentrated
  3. customthe residue was partitioned between 2N NaOH and CH2Cl2
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas recrystallized from ethanol (EtOH)

Sources & evidence

ORD record
ord-db082f9742f24417814a613ad2f85c60
Source dataset
uspto-grants-1998_02
Patent number
US05721255

Reaction notes

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