Benzyl Bromide → HCID 21462995, compound

HRID 1940558Notes

Reaction equation

HRID 1940558 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH3:2].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+]>CN(C)C=O.C(O)C>[CH2:9]([N:6]1[CH2:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH2:4][CH2:5]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 108224-EthylpyridineHCID 4311764Sodium borohydride

Product 1

HCID 21462995HCID 21462995, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-ethylpyridine (3.0 g, 28 mmol) in anhydrous dimethylformamide (10 ml) was treated with benzyl bromide (3.7 ml, 31 mmol) and the mixture was stirred at room temperature for two hours. The reaction mixture was diluted with absolute ethanol (60 ml), treated with sodium borohydride (1.3 g, 35 mmol) and stirred at reflux for one hour. The solvent was evaporated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed with 1:1 hexane/ethyl acetate as eluant to give the title compound (1.92 g, 34% over two steps) as a colourless oil; δH (CDCl3) 1.00 (3H, t, J 7.5 Hz, CH2CH3), 1.94-2.12 (4H, m, CH2CH3 and tetrahydropyridinyl CH2), 2.55 (2H, t, J 6.3 Hz, tetrahydropyridinyl CH2), 2.90-3.00 (2H, m, tetrahydropyridinyl CH2), 3.58 (2H, s, PhCH2N), 5.32-5.40 (1H, m, tetrahydropyridinyl 5-H), and 7.20-7.40 (5H, m, ArH); m/z (CI+, NH3) 202 (M+1)+.

Workup

  1. stirringstirred
  2. temperatureat reflux for one hour
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between dichloromethane and water
  5. customThe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was chromatographed with 1:1 hexane/ethyl acetate as eluant

Sources & evidence

ORD record
ord-90ed90dd3f11426d87ec7938429d06db
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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