Pyridine → HCID 12247535, compound

HRID 1402371Notes

Reaction equation

HRID 1402371 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.N1C=CC=CC=1.[Cl:15][C:16](Cl)([O:18]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:5]12[N:8]([C:16]([Cl:15])=[O:18])[CH:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 1360978-Azabicyclo(3.2.1)octane

Product 1

HCID 12247535HCID 12247535, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (10° C.) solution 8-aza-bicyclo[3.2.1]octane (295 mg, 2.00 mmol) and pyridine (486 μL, 6.02 mmol) in DCM (10 mL) was added triphosgene (595 mg, 2.00 mmol) portionwise. The reaction was allowed to reach room temperature and stirred overnight. The mixture was quenched with HCl (1M aqueous, 10 mL) and stirred for 30 min. The aqueous phase was extracted with DCM (×3) and the combined organic layers were washed with HCl (1M aqueous), brine, dried (MgSO4) and concentrated in vacuo, to give the title compound (244 mg, 70%). 1H NMR (400 MHz, CDCl3): 1.46-1.70 (4H, m), 1.72-1.92 (5H, m), 2.04-2.11 (2H, m), 4.39-4.44 (2H, m).

Workup

  1. customto reach room temperature
  2. customThe mixture was quenched with HCl (1M aqueous, 10 mL)
  3. stirringstirred for 30 min
  4. extractionThe aqueous phase was extracted with DCM (×3)
  5. washthe combined organic layers were washed with HCl (1M aqueous), brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ef32beddf8b4b9586bb27c7e332323a
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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