Acetone → HCID 53814823, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][CH2:9][NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH:2]=1.Cl.[CH3:18][C:19]([CH3:21])=O>>[CH2:21]([N:10]([CH2:9][CH:8]=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])[CH:19]=[CH2:18]Participants
Procedure
14.0 g (51.8 mmol) of N-allyl-N-[3-(3-pyridyl)[-allyl]-2,2,2-trifluoroacetamide were dissolved in 1.40 ml of acetone, and 30 ml of 10% strength aqueous hydrochloric acid were added and the mixture was irradiated under nitrogen in a boro-silicate glass apparatus at room temperature with a 150 watt high-pressure mercury lamp for 48 h. The reaction solution was then concentrated, taken up in 150 ml of water and adjusted to pH 8-9 with aqueous ammonia solution. The aqueous phase was extracted twice with tert-butyl methyl ether, and the combined organic phases were dried over sodium sulfate and concentrated. The residue was fractionated by column chromatography (silica gel, methylene chloride+2% methanol) to yield 6.2 g (42%) of unchanged N-allyl-N-[3- (3-pyridyl)allyl]-2,2,2-trifluoroacetamide and 3.7 g (26%) of 2,2,2-trifluoro-1-[exo-6-(3-pyridyl) -3-azabicyclo[3.2.0]hept-3-yl]ethanone as a dark oil.
Workup
- customthe mixture was irradiated under nitrogen in a boro-silicate glass apparatus at room temperature with a 150 watt high-pressure mercury lamp for 48 h
- concentrationThe reaction solution was then concentrated
- extractionThe aqueous phase was extracted twice with tert-butyl methyl ether
- dry with materialthe combined organic phases were dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bfee6a7ff1344888929750ff64c85e6e
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05521209
Reaction notes
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