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

HRID 1359358Notes

Reaction equation

HRID 1359358 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-ethylenedioxypyrrolidine-1-yl)pyridine, 240 mg of 1,3-bis (diphenylphosphino)propanenickel (II) chloride and 20 ml of tetrahydrofuran was stirred in an ice bath in a nitrogen atmosphere. Into the mixture were 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 at room temperature overnight as it was. The reaction solution was partitioned between an aqueous saturated ammonium chloride solution and ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography using 5-10% ethyl acetate/hexane, to give 6.6 g of the target compound.

Workup

  1. stirringby stirring at room temperature overnight as it
  2. customThe reaction solution was partitioned between an aqueous saturated ammonium chloride solution and ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-79150b776aed4c589b81009d95e16a17
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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