Benzyl Bromide → HCID 21462998, compound

HRID 1940553Notes

Reaction equation

HRID 1940553 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+]>CN(C)C=O.C(O)C>[CH2:14]([N:1]1[CH2:6][CH:5]=[C:4]([CH2:7][CH2:8][C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[CH2:3][CH2:2]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 21462997HCID 21462997, compound

Product 1

HCID 21462998HCID 21462998, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(pyridin-4-yl)-2-(furan-2-yl)ethane (2 g, 11.6 mmol) in anhydrous dimethylformamide (5 ml) was treated with benzyl bromide (1.5 ml, 12.7 mmol) and the reaction stirred at room temperature for one hour. The reaction was diluted with ethanol (50 ml), treated with sodium borohydride (0.55 g, 14.5 mmol) and heated at reflux for one hour. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic was separated, dried (Na2SO4) and evaporated to give crude product as a yellow oil. This material was triturated with diethyl ether to afford the title compound (2.3 g, 68%) as a colourless solid; δH (DMSO-d6) 1.92-2.10 (2H, m, tetrahydropyridinyl CH2), 2.14-2.30 (2H, m, CH2), 2.36-2.50 (2H, m, CH2), 2.60-2.82 (2H, m, tetrahydropyridinyl CH2), 2.84-2.90 (2H, m, tetrahydropyridinyl CH2), 3.50 (2H, br s, PhCH2N), 5.32-5.44 (1H, m, tetrahydropyridinyl 5-H), 6.02-6.10 (1H, m, furanyl H), 6.30-6.36 (1H, m, furanyl H), 7.16-7.36 (5H, m, ArH), and 7.44-7.52 (1H, m, furanyl H); m/z (CI+, NH3) 268 (M+1)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for one hour
  3. customThe solvent was evaporated
  4. customthe residue partitioned between ethyl acetate and water
  5. customThe organic was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give crude product as a yellow oil
  9. customThis material was triturated with diethyl ether

Sources & evidence

ORD record
ord-41f6f8ae735842f8849f9ec187c62d83
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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