Sodium Hydroxide → 6-Phenyl-7-oxa-3-azabicyclo[4.1.0]heptane

HRID 895047Notes

Reaction equation

HRID 895047 reaction equation
BrBr.[Br-].[Na+].Br.[C:6]1([C:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-:18].[Na+]>O>[O:18]1[C:12]2([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:13]1[CH2:14][NH:15][CH2:16][CH2:17]2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 253881Sodium BromideHCID 205741144-Phenyl-1,2,5,6-tetrahydropyridine hydrobromide

Product 1

HCID 129293756-Phenyl-7-oxa-3-azabicyclo[4.1.0]heptane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 33.6 g of bromine and 60 g of sodium bromide in 450 ml of water was added dropwise with stirring to solution comprising 50 g of 4-phenyl-1,2,5,6-tetrahydropyridine hydrobromide in 600 ml of water and the reaction mixture was then stirred at room temperature for 30 minutes. The solution was stirred on an ice bath while 252 ml of 10% sodium hydroxide was added dropwise thereto. The resulting mixture then being stirred at room temperature for a further 30 minutes. The aqueous solution was extracted with methylene chloride and the organic phase solution dried over sodium sulfate and then concentrated in vacuo to give 25.2 g of the desired 3,4-epoxy-4-phenyl piperidine as an oil.

Workup

  1. additionwas added dropwise
  2. stirringThe resulting mixture then being stirred at room temperature for a further 30 minutes
  3. extractionThe aqueous solution was extracted with methylene chloride
  4. dry with materialthe organic phase solution dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-672e5faeeda843dba3654189040b632c
Source dataset
uspto-grants-1981_08
Patent number
US04286095

Reaction notes

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