Benzyl Bromide → HCID 21462993, compound

HRID 1940557Notes

Reaction equation

HRID 1940557 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=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:11]1[CH2:10][CH:9]=[C:8]([CH2:7][CH2:6][CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)[CH2:13][CH2:12]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 21463007HCID 21463007, compound

Product 1

HCID 21462993HCID 21462993, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2-[tetrahydrofuran-2-yl]ethyl)pyridine (3.0 g, 16.9 mmol) in anhydrous dimethylformamide (5 ml) was treated with benzyl bromide (2.2 ml, 18.6 mmol) and the mixture was stirred at room temperature for one hour. The reaction was diluted with absolute ethanol (100 ml), treated with sodium borohydride (0.8 g, 21.2 mmol) and stirred at reflux for one hour. The solvent was evaporated in vacuo and the residue partitioned between diethyl ether and water. The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed with 3% methanol in dichloromethane as eluant to afford the title compound (3.75 g, 82%) as a colourless oil; δH (DMSO-d6) 1.30-2.08 (8H, m, 4×CH2), 2.45-2.52 (2H, m, tetrahydropyridinyl CH2), 2.52-2.56 (2H, m, CH2), 2.60-2.66 (2H, m, tetrahydropyridinyl CH2), 3.50 (2H, s, PhCH2N), 3.52-3.80 (3H, m, tetrahydrofuranyl CH2 and CH), 5.50-5.55 (1H, m, tetrahydropyridinyl 5-H), and 7.20-7.34 (5H, m, ArH); m/z (CI+, NH3) 272 (M+1)+.

Workup

  1. stirringstirred
  2. temperatureat reflux for one hour
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between diethyl ether and water
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was chromatographed with 3% methanol in dichloromethane as eluant

Sources & evidence

ORD record
ord-1357f0e45f8c475ca79ca42e8197550c
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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