1,3-Cyclohexadiene → 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene hydrochloride

HRID 652079Notes

Reaction equation

HRID 652079 reaction equation
[Cl:1][C:2]1([N:8]=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1CCC=CC=1>C(O)C.C(Cl)(Cl)(Cl)Cl>[ClH:1].[CH:5]12[CH2:6][CH2:7][CH:2]([CH:3]=[CH:4]1)[NH:8][O:9]2

Participants

5

Reactant 2

HCID 116051,3-CyclohexadieneHCID 6375621-Chloro-1-nitrosocyclohexane

Product 1

HCID 126498822-Oxa-3-azabicyclo[2.2.2]oct-5-ene hydrochlorideYield 73.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 6.1 g of 1-chloro-1-nitrosocyclohexane in 135 ml of ethanol and 260 ml of carbon tetrachloride, cooled to -20° C. in an acetone-dry ice bath, was slowly added 33.6 ml of 1,3-cyclohexadiene. The mixture was stored at -20° C. for 6 days and the solid collected, giving 4.5 g of 2-oxa-3-azabicyclo[2.2.2]oct-5-ene, hydrochloride.

Workup

  1. customthe solid collected

Sources & evidence

ORD record
ord-17b3f874509149bc81a84e0db28d1dd5
Source dataset
uspto-grants-1987_06
Patent number
US04670458

Reaction notes

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