Cyanuric chloride → 3-(4,6-Dichloro-1,3,5-triazin-2-yl)-8-oxa-3-azabicyclo[3.2.1]octane
Reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].Cl.[CH:11]12[O:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][NH:13][CH2:12]2>CC(C)=O.O.C([O-])(O)=O.[Na+]>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([N:13]2[CH2:12][CH:11]3[O:18][CH:15]([CH2:16][CH2:17]3)[CH2:14]2)[N:7]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a solution of cyanuric chloride (2.00 g, 10.85 mmoles) in acetone (20 mL) and water (10 mL) at 0° C. was added a solution of 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (1.46 g, 9.76 mmoles) in saturated aqueous NaHCO3 (25 mL) and acetone (25 mL) via addition funnel over 15 minutes. The reaction was stirred at 0° C. for 2 hours, then filtered to collect a white precipitate. The precipitate was washed with water (25 mL) and dried. The crude product was purified by column chromatography (30:70 ethyl acetate in hexanes) to provide 3-(4,6-dichloro-1,3,5-triazin-2-yl)-8-oxa-3-azabicyclo[3.2.1]octane (1.55 g) as a white solid.
Workup
- additionvia addition funnel over 15 minutes
- filtrationfiltered
- customto collect a white precipitate
- washThe precipitate was washed with water (25 mL)
- customdried
- customThe crude product was purified by column chromatography (30:70 ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-239a3185a1804ef7b525ee31443b9fa5
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445486B2
Reaction notes
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