3-Phenylpyridine → 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-5-phenyl-1,2,3,6-tetrahydropyridine

HRID 2407224Notes

Reaction equation

HRID 2407224 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[C:13]1([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+]>C1(C)C(C)=CC=CC=1.CO>[O:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH:3]1[CH2:2][N:21]1[CH2:20][C:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 138863-PhenylpyridineHCID 983332-Bromomethyl-1,4-benzodioxaneHCID 4311764Sodium borohydride

Product 1

HCID 251745131-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-5-phenyl-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7237O-XyleneSolvent

Procedure

A mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (500 mg, 2.18 mmol) and 3-phenyl-pyridine (339 mg, 2.18 mmol) in xylene (2 ml) was refluxed for 4 h. After cooling, the solvent was decanted to give the crude oily pyridinium salt, which was dissolved in MeOH (5 ml). NaBH4 (330 mg, 4 eq) was added in small portions to the cooled mixture. After stirring for 2 h at RT, MeOH was evaporated, water was added and the mixture extracted with EtOAc. Drying (Na2SO4) and evaporation gave the crude product, which was purified by flash chromatography (heptane/EtOAc).

Workup

  1. temperaturewas refluxed for 4 h
  2. temperatureAfter cooling
  3. customthe solvent was decanted
  4. customto give the crude oily pyridinium salt, which
  5. customMeOH was evaporated
  6. additionwater was added
  7. extractionthe mixture extracted with EtOAc
  8. customDrying
  9. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-94b5da3e13c74bfea8df06750f7b43c5
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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