Water → Xaliproden

HRID 1251328Notes

Reaction equation

HRID 1251328 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.Cl.[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.[OH-].[Na+].O>C(O)C>[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

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2282702-(2-Bromoethyl)naphthaleneHCID 234359914-(3-(Trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 128919XaliprodenYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12.5 g of 2-(2-bromoethyl)naphthalene, 14 g of 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride, 4.34 g of sodium hydroxide, 135 ml of water and 95 ml of 95% ethanol is heated for 5 hours under reflux, and the reaction mixture is then left to cool overnight to room temperature. The mixture is cooled to below 25° C., and then is filtered, the product thus isolated is washed with water and then dried in vacuo at 50° C. 1-[2-(2-naphthyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine base is thus obtained in a yield of 90% calculated on the starting 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride.

Workup

  1. temperatureis heated for 5 hours
  2. temperatureunder reflux
  3. waitthe reaction mixture is then left
  4. temperatureto cool overnight to room temperature
  5. temperatureThe mixture is cooled to below 25° C.
  6. filtrationis filtered
  7. customthe product thus isolated
  8. washis washed with water
  9. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-8bc1b2a695394c2ca3fada3974de7d6c
Source dataset
uspto-grants-2002_01
Patent number
US06342505B1

Reaction notes

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