Hydrochloric Acid → 4-(3-Trifluoromethylphenyl)-1-cyanomethyl-1,2,3,6-tetrahydropyridine hydrochloride

HRID 2308815Notes

Reaction equation

HRID 2308815 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]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 111280344-[3-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

Product 1

HCID 201878304-(3-Trifluoromethylphenyl)-1-cyanomethyl-1,2,3,6-tetrahydropyridine hydrochlorideYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

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

  1. temperatureis heated
  2. temperatureto reflux for 5 hours
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated
  5. customThe ethereal solution thus obtained
  6. filtrationis filtered
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customTo the solution thus obtained

Sources & evidence

ORD record
ord-dc7c90fadc9b4ffcb288acb6980cfb83
Source dataset
uspto-grants-1987_09
Patent number
US04691019

Reaction notes

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