Triethylamine → 1-[2-(6-Methyl-2-pyridyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

HRID 1248015Notes

Reaction equation

HRID 1248015 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.Cl.[Cl:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=1.C(N(CC)CC)C>C(O)C>[ClH:18].[CH3:27][C:23]1[N:22]=[C:21]([CH2:20][CH2:19][N:12]2[CH2:11][CH:10]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=3)[CH2:14][CH2:13]2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 205443Pyridine, 2-(2-chloroethyl)-6-methyl-, hydrochloride (1:1)HCID 111280344-[3-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

Product 1

HCID 202805261-[2-(6-Methyl-2-pyridyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochlorideYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

By operating as described in Example 1, 5.7 g of 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine are reacted with 5.2 g of 2-(2-chloroethyl)-6-methylpyridine hydrochloride in the presence of 7.5 ml of triethylamine in 60 ml of ethanol at reflux for 18 hours to obtain 3.5 g of 1-[2-(6-methyl-2-pyridyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride; m.p. 207°-210° C.

Workup

  1. temperatureat reflux for 18 hours

Sources & evidence

ORD record
ord-606ee38013914c88b06d16a834d9d509
Source dataset
uspto-grants-1985_06
Patent number
US04521428

Reaction notes

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