Hydrochloric Acid → HCID 68496449, compound

HRID 445245

Reaction equation

HRID 445245 reaction equation
C([N:8]1[CH:17]([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)C1C=CC=CC=1.[ClH:29]>CO.[Pd]>[ClH:29].[CH3:18][CH:17]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([F:27])([F:26])[F:28])=[CH:23][CH:24]=2)[NH:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 595362822-Benzyl-3-methyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 68496449HCID 68496449, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of 2-benzyl-3-methyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (485 mg, 1.27 mmol) in MeOH (5 mL) was added palladium, 10 wt. % on activated carbon (41 mg, 0.38 mmol). The resulting mixture was then stirred under H2 for 16 h. Then, 5 N HCl (0.2 mL) was added followed by palladium, 10 wt. % on activated carbon (41 mg, 0.38 mmol). The resulting mixture was stirred at RT under H2 (45 psi) for 30 min. The mixture was filtered through celite and the celite was washed with MeOH (2×5 mL). The combined filtrates were concentrated to give the title compound as a light yellow solid (HCl salt), which was used in the next step without further purification.

Workup

  1. stirringThe resulting mixture was stirred at RT under H2 (45 psi) for 30 min
  2. filtrationThe mixture was filtered through celite
  3. washthe celite was washed with MeOH (2×5 mL)
  4. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-8b290a7c96fc4c3ba073afaa60c6d4c6
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Linked notes

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