Triethylamine → Xaliproden hydrochloride

HRID 1953800Notes

Reaction equation

HRID 1953800 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.Br[CH2:25][CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1.[Cl:37]CCC1C=CC2C(=CC=CC=2)C=1>C(O)C>[ClH:37].[CH:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:35]=[CH:36][C:27]=1[CH2:26][CH2:25][N:12]1[CH2:11][CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2282702-(2-Bromoethyl)naphthaleneHCID 111280344-[3-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridineHCID 12698954HCID 12698954, compound

Product 1

HCID 128918Xaliproden hydrochlorideYield 59.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In two different preparations, 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine is reacted, in the presence of triethylamine, with 2-(2-bromoethyl)naphthalene (PREPARATION A) and respectively with 2-(2-chloroethyl)naphthalene (PREPARATION B) in ethanol under reflux for 20 hours. The reaction mixtures of the two preparations were concentrated, the residue was taken up with ethyl ether and the ether solution, which was filtered and washed with water, was dried and evaporated. The residue was taken up with a solution of gaseous hydrochloric acid in isopropanol to give 1-[2-(2-naphthyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride, which was crystallized from ethanol.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe reaction mixtures of the two preparations
  3. concentrationwere concentrated
  4. filtrationthe ether solution, which was filtered
  5. washwashed with water
  6. customwas dried
  7. customevaporated

Sources & evidence

ORD record
ord-7891de4724cf45bbad362ebdd627910b
Source dataset
uspto-grants-2000_09
Patent number
US06118006

Reaction notes

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