Sodium Carbonate → 7-[4,4-bis(4-fluorophenyl)butyl]hexahydro-3,3-dimethyl-1H-oxazolo[3,4-a]pyrazine
Reaction equation
I[CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH3:20][C:21]1([CH3:30])[N:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH:24]2[CH2:23][O:22]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:4][CH2:3][CH2:2][N:28]2[CH2:27][CH2:26][N:25]3[C:21]([CH3:30])([CH3:20])[O:22][CH2:23][CH:24]3[CH2:29]2)=[CH:7][CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 30.7 parts of 1,1'-(4-iodobutylidene)bis[4-fluorobenzene], 11.5 parts of hexahydro-3,3-dimethyl-1H-oxazolo-[3,4-a]pyrazine, 14.8 parts of sodium carbonate and 270 parts of N,N-dimethylformamide was stirred for 5 hours at about 70° C. The reaction mixture was cooled overnight to room temperature and the solvent was evaporated. The residue was dissolved in trichloromethane. The organic phase was washed with water, dried, filtered and evaporated, yielding 34 parts of 7-[4,4-bis(4-fluorophenyl)butyl]hexahydro-3,3-dimethyl-1H-oxazolo[3,4-a]pyrazine as a residue (intermediate 94).
Workup
- temperatureThe reaction mixture was cooled overnight to room temperature
- customthe solvent was evaporated
- dissolutionThe residue was dissolved in trichloromethane
- washThe organic phase was washed with water
- customdried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-9a4a2ed6582a47a48d6db76908c0db46
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04766125
Reaction notes
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