Benzyl Bromide → 2-Benzyl-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine

HRID 2216370

Reaction equation

HRID 2216370 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:12][CH2:11][C:10]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:9]2)[N:3]=1.[CH2:17]([Mg]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Br)C1C=CC=CC=1.[Mg]>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].C(OCC)C.O1CCCC1>[CH2:17]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:12][CH2:11][C:10]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:9]2)[N:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 5462224MagnesiumHCID 219422692-Bromo-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridineHCID 178419663HCID 178419663, compound

Product 1

HCID 219422622-Benzyl-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine

Reagents, catalysts & solvents 3

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chlorideCatalystHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6.3 g of 2-bromo-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine, 240 mg of 1,3-bis(diphenylphosphino)propanenickel (II) chloride and 20 ml of tetrahydrofuran was stirred in advance under nitrogen atmosphere in an ice bath. To this was added dropwise a diethyl ether solution of benzyl magnesium bromide prepared from 3.4 ml of benzyl bromide, 0.8 g of magnesium and 15 ml of diethyl ether, followed by stirring as it was at room temperature for overnight. The reaction mixture was partitioned between a saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography with 5–10% ethyl acetate/hexane, to give 6.6 g of the title compound.

Workup

  1. stirringby stirring as it
  2. customThe reaction mixture was partitioned between a saturated aqueous ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7efc740474614fa8bb53d2db1bac1da8
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Linked notes

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