Benzyl Bromide → HCID 67057591, compound

HRID 1510205Notes

Reaction equation

HRID 1510205 reaction equation
[CH:1]([O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH4-].[Na+]>C(#N)C>[CH:1]([O:14][CH2:15][CH2:16][C:17]1[CH2:18][CH2:19][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][CH:22]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 67057457HCID 67057457, compound

Product 1

HCID 67057591HCID 67057591, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

With reference to FIG. 7, 4-(2-(benzhydryloxy)ethyl)pyridine 3 (4.0 g, 13.82 mmol) and benzyl bromide (2.86 g, 16.73 mmol) were dissolved in 20 ml of dry acetonitrile and refluxed for 6 hrs. The solvent was removed in vacuo. After drying the residue for 2 hrs under high vacuum, it was dissolved in 30 ml of dry methanol and cooled in an ice-bath. Sodium borohydride (0.76 g, 20.05 mmol) was then added very slowly portionwise over a period of 1.5 hrs, and the solution was gradually brought to room temperature. The reaction was quenched with water after stirring for 4 h, and methanol was removed in vacuo. The residual product was dissolved in ethyl acetate, washed with water, dried (Na2SO4), and concentrated. The crude product was purified by column chromatography over silica gel (hexane:ethyl acetate 5:1) to produce 4 (5.0 g, 94%) as a colorless oil. 1H-NMR (CDCl3; 400 MHz): 2.086 (brs, 2H, H-3), 2.32-2.35 (t, 2H, J=6.8 Hz, OCH2CH2), 2.52-2.54 (t, 2H, J=5.6 Hz, H-2), 2.94-2.94 (brm, 2H, H-6) 3.52-3.55 (m, 4H, NCH2Ph, OCH2CH2), 5.34 (s, 1H, PhCH(O)Ph), 5.41-5.42 (brs, 1H, CH═C), 7.12-7.37 (m, 15H, ArH).

Workup

  1. temperaturerefluxed for 6 hrs
  2. customThe solvent was removed in vacuo
  3. customAfter drying the residue for 2 hrs under high vacuum, it
  4. dissolutionwas dissolved in 30 ml of dry methanol
  5. temperaturecooled in an ice-bath
  6. customwas gradually brought to room temperature
  7. customThe reaction was quenched with water
  8. custommethanol was removed in vacuo
  9. dissolutionThe residual product was dissolved in ethyl acetate
  10. washwashed with water
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated
  13. customThe crude product was purified by column chromatography over silica gel (hexane:ethyl acetate 5:1)

Sources & evidence

ORD record
ord-bf850195680c4f158a45662946bd07fb
Source dataset
uspto-grants-2012_07
Patent number
US08211916B2

Reaction notes

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