Benzyl Bromide → HCID 178419828, compound

HRID 1816958Notes

Reaction equation

HRID 1816958 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)=[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:3]2[CH:4]=[CH:5][NH:1][N:2]=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 178419957HCID 178419957, compound

Product 1

HCID 178419828HCID 178419828, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a hot (80° C.) solution of 4-(1H-pyrazol-3-yl)pyridine (9.6 g) in 2-propanol (60 mL) was added benzyl bromide (20 mL, 2.5 equiv.) and the resulting mixture was 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 (13 g) was added in several portions over 30 minutes, and the mixture was stirred for an additional 30 minutes. The reaction was quenched by the careful addition of water, the ethanol was removed by evaporation, and the residue was partitioned between dichloromethane and water. The organic layer was dried over MgSO4, filtrated and evaporated to give 1-benzyl-4-(1H-pyrazol-3-yl)-1,2,3,6-tetrahydropyridine (16 g)

Workup

  1. temperaturethe resulting mixture was 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 (13 g) was added in several portions over 30 minutes
  9. customThe reaction was quenched by the careful 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. customevaporated

Sources & evidence

ORD record
ord-36161a45e37b4ef1b58e1472170205e5
Source dataset
uspto-grants-2009_10
Patent number
US07598243B2

Reaction notes

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