3-(2-Methoxybenzylamino)-2-phenylpyridine → CP-99994

HRID 1376818Notes

Reaction equation

HRID 1376818 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C:7]1[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][CH:10]=[CH:11][CH:12]=1>C(O)(=O)C.[Pt]=O>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C@H:7]1[CH2:12][CH2:11][CH2:10][NH:9][C@H:8]1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 152327123-(2-Methoxybenzylamino)-2-phenylpyridine

Product 1

HCID 5311057CP-99994Yield 58.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

3-(2-Methoxybenzylamino)-2-phenylpyridine (25 mg) was dissolved in 3 mL of acetic acid. To this solution was added 3 mg of platinum oxide and the mixture was placed on a Parr apparatus (35-40 p.s.i. H2) for ca. 2.5 hours. During this period, three additional 2.5 mg portions of catalyst were added to the system. The mixture was filtered through Celite® which had been rinsed well with ethanol and the filtrate was concentrated with a rotary evaporator. The residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate, the layers were separated and the aqueous phase was extracted with three portions of CH2Cl2. The combined organic fractions were dried (Na2SO4) and concentrated to afford 15 mg of the title compound contaminated with a trace of 3-(2-methoxy-benzylamino)-2-phenylpyridine and a trace of material in which the 2-phenyl substituent had been reduced to a cyclohexyl moiety. The material prepared in this manner has spectral properties identical to those of the free base of the title compound of Example 1C.

Workup

  1. waitDuring this period
  2. additionthree additional 2.5 mg portions of catalyst were added to the system
  3. filtrationThe mixture was filtered through Celite® which
  4. washhad been rinsed well with ethanol
  5. concentrationthe filtrate was concentrated with a rotary evaporator
  6. customThe residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  7. customthe layers were separated
  8. extractionthe aqueous phase was extracted with three portions of CH2Cl2
  9. dry with materialThe combined organic fractions were dried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b1f9721ba5a6461b9dabad85500aad0e
Source dataset
uspto-grants-1997_09
Patent number
US05663349

Reaction notes

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