Potassium Carbonate → Xaliproden hydrochloride

HRID 1953798Notes

Reaction equation

HRID 1953798 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.[ClH:14].[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([C:23]2[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=2)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[ClH:14].[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][CH2:2][N:26]1[CH2:25][CH:24]=[C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:29])[F:30])[CH:18]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2282702-(2-Bromoethyl)naphthaleneHCID 234359914-(3-(Trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 128918Xaliproden hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.25 g of 2-(2-bromoethyl)naphthalene, 7 g of 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride, 3.75 g of potassium carbonate and 100 ml of acetone is refluxed for 4 hours and the reaction mixture is then allowed to cool to room temperature. The salts formed are filtered off and discarded. The solvent is evaporated off and the residue is taken up with a solution of hydrochloric acid in ethanol to give 1-[2-(2-naphthyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride, which is recrystallized from ethanol. Yield: 70% of theory, relative to the starting 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride. The product obtained is in the form of a fine white crystalline powder having an HPLC purity of 99.9%.

Workup

  1. temperatureis refluxed for 4 hours
  2. customThe salts formed
  3. filtrationare filtered off
  4. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-9b835bdd656842ea850982e12c601155
Source dataset
uspto-grants-2000_09
Patent number
US06118006

Reaction notes

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