Hydrochloric Acid → HCID 67455002, compound

HRID 1400192Notes

Reaction equation

HRID 1400192 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:26])[C:13]2[CH:18]=[CH:17][CH:16]=[N:15][C:14]=2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C(O)C.[Pt]=O>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH:14]2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[O:26])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59376169HCID 59376169, compound

Product 1

HCID 67455002HCID 67455002, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(3-tert-butylphenyl)-2-(3-fluorophenyl)nicotinamide (501.2 mg, 1.4 mmol), platinum oxide (51.9 mg, 0.21 mmol), and concentrated HCl (400 μL, 5.2 mmol) in 5 mL of ethanol was stirred vigorously under hydrogen balloon overnight. The mixture was filtered, and the solids washed with 25 mL of methanol three times. The combined solution was dried under reduced pressure. To the residue was added 30 mL of saturated sodium bicarbonate and 150 mL of EtOAc. The organic layer was separated, and dried over sodium sulfate. Evaporation of solvent gave the crude 2-(3-fluorophenyl)piperidine-3-carboxylic acid (3-tert-butylphenyl)amide as a brown solid, which was taken on directly to the next step. MS: (ES) m/z 355.7 (M+H+).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids washed with 25 mL of methanol three times
  3. customThe combined solution was dried under reduced pressure
  4. additionTo the residue was added 30 mL of saturated sodium bicarbonate and 150 mL of EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-b80d8b8b75d5415ab9a579dd60f7fb37
Source dataset
uspto-grants-2014_12
Patent number
US08906938B2

Reaction notes

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