Benzyl Bromide → 1,2,3,6-Tetrahydro-1-(phenylmethyl)-4-(1H-pyrazol-4-yl)pyridine

HRID 1725763Notes

Reaction equation

HRID 1725763 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[CH:3]=[N:2]1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(O)C>[CH2:12]([N:9]1[CH2:10][CH:11]=[C:6]([C:4]2[CH:5]=[N:1][NH:2][CH:3]=2)[CH2:7][CH2:8]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 14178904-(1H-pyrazol-4-yl)pyridine

Product 1

HCID 690533111,2,3,6-Tetrahydro-1-(phenylmethyl)-4-(1H-pyrazol-4-yl)pyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a hot (80° C.) solution of 4-(1H-pyrazol-4-yl)pyridine (4.8 g) in 2-propanol was added benzyl bromide (10 mL, 2.5 equiv.) and the resulting mixture heated at reflux for 10 minutes. After cooling in an ice bath, the precipitate was filtered and washed with more 2-propanol and air dried. The solid was suspended in ethanol at 0° C. and sodium borohydride (6.5 g) was added in several portions over 30 minutes, and the mixture was stirred for an additional 30 minutes. The reaction was quenched by carefully addition of water, and the ethanol was removed by evaporation, and the residue was partitioned between dichloromethane and water. The organic layer was dried over MgSO4, and filtrated and evaporation gives 1-benzyl-4-(1H-pyrazol-4-yl)-1,2,3,6-tetrahydropyridine (7.5 g)

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 10 minutes
  3. temperatureAfter cooling in an ice bath
  4. filtrationthe precipitate was filtered
  5. washwashed with more 2-propanol and air
  6. customdried
  7. customwas suspended in ethanol at 0° C.
  8. additionsodium borohydride (6.5 g) was added in several portions over 30 minutes
  9. customThe reaction was quenched by carefully addition of water
  10. customthe ethanol was removed by evaporation
  11. customthe residue was partitioned between dichloromethane and water
  12. dry with materialThe organic layer was dried over MgSO4
  13. filtrationfiltrated
  14. customevaporation

Sources & evidence

ORD record
ord-ca09603156c74cd3a62dcdc90c914e27
Source dataset
uspto-grants-2009_02
Patent number
US07491737B2

Reaction notes

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