Hydrochloric Acid → 4-(3-Trifluoromethylphenyl)-1-cyanomethyl-1,2,3,6-tetrahydropyridine hydrochloride
Reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:17]([N:19](CC)CC)[CH3:18].[Cl:24]CC#N.Cl>C(O)C.C(O)(C)C>[ClH:24].[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][CH2:13][N:12]([CH2:18][C:17]#[N:19])[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 0.025 mole of 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine, 3.5 ml of triethylamine and 0.025 mole of chloroacetonitrile in 40 ml of ethanol is heated to reflux for 5 hours. The reaction mixture is cooled, concentrated and the residue is taken up with diethyl ether. The ethereal solution thus obtained is filtered, washed with water and dried over anhydrous sodium sulfate. To the solution thus obtained is added a saturated solution of hydrogen chloride in isopropanol. In this way, the 4-(3-trifluoromethylphenyl)-1-cyanomethyl-1,2,3,6-tetrahydropyridine hydrochloride is obtained which, after crystallization in isopropanol, melts at 169°-172° C. Yield 75% of the theoretical.
Workup
- temperatureis heated
- temperatureto reflux for 5 hours
- temperatureThe reaction mixture is cooled
- concentrationconcentrated
- customThe ethereal solution thus obtained
- filtrationis filtered
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- customTo the solution thus obtained
Sources & evidence
- ORD record
- ord-904951467fce46fda12d161e926c19b8
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04602024
Reaction notes
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