Benzyl Bromide → 1-Benzyl-4-(2-pyridyl)-1,2,3,6-tetrahydropyridine

HRID 380483Notes

Reaction equation

HRID 380483 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH4-].[Na+]>CN(C=O)C.CC#N>[CH2:13]([N:10]1[CH2:11][CH:12]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:8][CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 684882,4'-BipyridineHCID 4311764Sodium borohydride

Product 1

HCID 151233351-Benzyl-4-(2-pyridyl)-1,2,3,6-tetrahydropyridineYield 99.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A Solution of 2 g (12.8 mmol) of 4-(2-pyridyl)pyridine (Aldrich) and 2.18 g (12.8 mmol) of benzylbromide in 15 mL of DMF and 15 mL of CH3CN was stirred at 95° C. for 4 h. The reaction mixture was then concentrated and redissolved in 20 mL of methanol. To the reaction mixture at 0° C. was added 0.95 g, (25.6 mmol) of NaBH4 and the reaction mixture was stirred for 1 h. The reaction was quenched with 6N HCl, and was partitioned between CH2Cl2 and 1N NaOH. The aqueous layer was extracted 3 times with CH2Cl2, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified chomatography [silica, CH2Cl2:ethyl acetate:(2M NH3 in MeOH), 100:100:2] to give 3.2 g of the title compound.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionredissolved in 20 mL of methanol
  3. customThe reaction was quenched with 6N HCl
  4. customwas partitioned between CH2Cl2 and 1N NaOH
  5. extractionThe aqueous layer was extracted 3 times with CH2Cl2
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified chomatography [silica, CH2Cl2:ethyl acetate:(2M NH3 in MeOH), 100:100:2]

Sources & evidence

ORD record
ord-e47691f9f4c8464d880ff0279238f206
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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