Water → Xaliproden

HRID 1698839Notes

Reaction equation

HRID 1698839 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 refluxed for 5 hours and the reaction mixture is then allowed to cool to room temperature overnight. It is cooled to below 25° C. and then filtered and the product isolated in this way is washed with water and dried under vacuum at 50° C. to give 1-[2-(naphth-2-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine base with a yield of 90%, calculated relative to the starting 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride.

Workup

  1. temperatureis refluxed for 5 hours
  2. temperatureIt is cooled to below 25° C.
  3. filtrationfiltered
  4. customthe product isolated in this way
  5. washis washed with water
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-8d66d163946f4fa2ab1ecd0f26fec2d2
Source dataset
uspto-grants-2002_02
Patent number
US06344464B1

Reaction notes

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