1,4-Dioxane hydrochloride → HCID 67266296, compound

HRID 1465442Notes

Reaction equation

HRID 1465442 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH:12]3[CH2:14][CH:9]2[CH2:10][N:11]3C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.O1CCOCC1.[ClH:28]>O1CCOCC1>[ClH:28].[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH:12]3[CH2:14][CH:9]2[CH2:10][NH:11]3)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58181232HCID 58181232, compound

Product 1

HCID 67266296HCID 67266296, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 5-(4-iodophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (335 mg, 0.84 mmol) in anhydrous dioxane (3 ml) was added 4M-hydrogen chloride dioxane solution (4 ml, 16 mmol). After stirring at room temperature for 2 hrs, the mixture was concentrated under reduced pressure, dichloromethane was added and the mixture was concentrated again. The residue was washed with diethyl ether and dichloromethane, and dried to give 5-(4-iodophenyl) -2,5-diazabicyclo[2.2.1]heptane hydrochloride (272 mg, 96%) as a pale-green solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure, dichloromethane
  2. additionwas added
  3. concentrationthe mixture was concentrated again
  4. washThe residue was washed with diethyl ether and dichloromethane
  5. customdried

Sources & evidence

ORD record
ord-5c512969a3604330a298eb774df623f1
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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