Hydrochloric Acid → 1-Methyl-4-ethynyl-4-(2-nitrophenoxy)piperidine hydrochloride
Reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][C:7]([C:11]#[CH:12])([OH:10])[CH2:6][CH2:5]1.F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].[ClH:23]>CS(C)=O.O>[ClH:23].[CH3:3][N:4]1[CH2:9][CH2:8][C:7]([C:11]#[CH:12])([O:10][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])[CH2:6][CH2:5]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of 0.58 g of sodium hydride (59% in oil; washed three times with hexanes) in 15 ml of dimethylsulfoxide was heated at 80°-90° for 0.5 hour under nitrogen. The resultant solution was cooled in an ice bath and 2.0 g of 1-methyl-4-ethynyl-4-hydroxypiperidine was added. After five min, the mixture was cooled to 0° and a solution of 2.4 g of 2-fluoronitrobenzene was added dropwise. The mixture was stirred 1 hr at 0°, 3 hrs at room temperature, poured into water, extracted twice with ether, washed with saturated sodium chloride solution and dried over anhydrous potassium carbonate. Filtration followed by evaporation of the solvent provided an oil, which was treated with ethereal hydrogen chloride to yield 2.34 g (54.8%) of product.
Workup
- temperaturewas heated at 80°-90° for 0.5 hour under nitrogen
- temperaturethe mixture was cooled to 0°
- extractionextracted twice with ether
- washwashed with saturated sodium chloride solution
- dry with materialdried over anhydrous potassium carbonate
- filtrationFiltration
- customfollowed by evaporation of the solvent
- customprovided an oil, which
Sources & evidence
- ORD record
- ord-ec51712055bc4e39a2f162e3c1fa0c5d
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04788201
Reaction notes
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