Xaliproden hydrochloride → HCID 19099578, compound

HRID 1975313Notes

Reaction equation

HRID 1975313 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>[Pd].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[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 128918Xaliproden hydrochloride

Product 1

HCID 19099578HCID 19099578, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-[2-(2-naphtyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride (5 g, 0.012 mol), 10% Pd/C (0.6 g) and 95% ethanol (130 ml) are charged into a hydrogenation reaction vessel and hydrogenated, under stirring, at 50° C. for 3 hours. The catalyst is then removed by filtration and the filtrate is concentrated to dryness. The residue is triturated with a small amount of diethyl ether and the white solid which is obtained therefrom by filtration is crystallised from absolute ethanol (120 ml) and dried affording 3.5 g (0.0083 mol) of 1-[2-(2-naphthyl)ethyl]-4-(3-trifluoromethylphenyl)piperidine hydrochloride. M.p. 296°-298° C.

Workup

  1. additionare charged into a hydrogenation reaction vessel
  2. customThe catalyst is then removed by filtration
  3. concentrationthe filtrate is concentrated to dryness
  4. customThe residue is triturated with a small amount of diethyl ether
  5. customthe white solid which is obtained
  6. filtrationby filtration
  7. customis crystallised from absolute ethanol (120 ml)
  8. customdried

Sources & evidence

ORD record
ord-906c3d98e5fa46f4821b8437a9082096
Source dataset
uspto-grants-1994_02
Patent number
US05286734

Reaction notes

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