Formic Acid → 1-Formyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine
Reaction equation
[CH:1](O)=[O:2].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[F:28][C:29]1[C:41]([F:42])=[C:40]([F:43])[C:39]([F:44])=[C:38]([F:45])[C:30]=1[O:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(=O)(O)[O-].[Na+]>C(OCC)C.O>[CH:1]([N:35]1[CH2:36][CH2:37][CH:32]([O:31][C:30]2[C:38]([F:45])=[C:39]([F:44])[C:40]([F:43])=[C:41]([F:42])[C:29]=2[F:28])[CH2:33][CH2:34]1)=[O:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 55 °C
Procedure
A mixture of 1.5 ml of formic acid and 3.5 ml of acetic anydride was stirred at 55° C. for one hour, cooled, and treated with a solution of 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine in 50 ml of diethyl ether. The reaction mixture was then stirred at ambient temperature for three hours. Thereafter, the mixture was poured into 100 ml of water, adjusted to pH 10 by the addition of sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated solution of chloride and dried over anhydrous magnesium sulfate. Filtration, followed by evaporation of the solvent afforded an oil which was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate) to yield 4.0 g (91%) of 1-formyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine, m.p. 32°-34° C.
Workup
- temperaturecooled
- stirringThe reaction mixture was then stirred at ambient temperature for three hours
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationFiltration
- customfollowed by evaporation of the solvent
- customafforded an oil which
- customwas purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate)
Sources & evidence
- ORD record
- ord-de14a4d7a020427c9b58af4c229c58ca
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212184
Reaction notes
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