Water → Xaliproden

HRID 1953797Notes

Reaction equation

HRID 1953797 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, the reaction mixture is subsequently allowed to cool to room temperature overnight 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-(2-naphthyl)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. filtrationfiltered
  3. customthe product isolated in this way
  4. washis washed with water
  5. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-29ef98f065304edfbc58b7197dbd4d24
Source dataset
uspto-grants-2000_09
Patent number
US06118006

Reaction notes

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