Hydrochloric Acid → Xaliproden hydrochloride

HRID 1953799Notes

Reaction equation

HRID 1953799 reaction equation
[ClH:1].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][N:14]1[CH2:19][CH:18]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH2:16][CH2:15]1>C(O)C>[ClH:1].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][N:14]1[CH2:15][CH:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 128919Xaliproden

Product 1

HCID 128918Xaliproden hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

6.25 ml of concentrated hydrochloric acid are added, with stirring, to a solution of 17.2 g of 1-[2-(2-naphthyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine base, obtained according to Example 1, in 200 ml of absolute ethanol. The resulting mixture is refluxed for 90 minutes, after which the solution is first filtered hot and then evaporated to remove about 100 ml of solvent. 20 ml of distilled water are added to the mixture, the temperature of the solution is brought to 75° C. and said solution is then cooled to 5° C. at a rate of 10° C. per hour. The mixture is kept at 5° C. for about one hour and the product is then collected by filtration and washed with a mixture of 32 ml of absolute ethanol and 3 ml of water. The product is dried under vacuum at 50° C. to give 1-[2-(2-naphthyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride.

Workup

  1. customobtained
  2. temperatureThe resulting mixture is refluxed for 90 minutes
  3. customevaporated
  4. customto remove about 100 ml of solvent
  5. addition20 ml of distilled water are added to the mixture
  6. customis brought to 75° C.
  7. filtrationthe product is then collected by filtration
  8. washwashed with a mixture of 32 ml of absolute ethanol and 3 ml of water
  9. customThe product is dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-18adf6079da948fd9597936167d93860
Source dataset
uspto-grants-2000_09
Patent number
US06118006

Reaction notes

Loading…