Tetrahydrofuran → 2-Chloro-4-[4-(4-fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1,3,5-triazine

HRID 1477677Notes

Reaction equation

HRID 1477677 reaction equation
O1CCCC1.Cl.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH:19]=2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:26][C:27]1[N:32]=[C:31](Cl)[N:30]=[CH:29][N:28]=1>C(OCC)(=O)C.O>[Cl:26][C:27]1[N:32]=[C:31]([N:17]2[CH2:16][CH2:15][C:14]([C:11]3[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=3)=[CH:19][CH2:18]2)[N:30]=[CH:29][N:28]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 178102,4-Dichloro-1,3,5-triazineHCID 1977474-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 1178392512-Chloro-4-[4-(4-fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1,3,5-triazineYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran (10 mL)-water (4.0 mL) solution of 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (1.43 g, 6.67 mmol) and sodium carbonate (1.56 g, 14.7 mol), 2,4-dichloro-1,3,5-triazine (1.00 g, 6.67 mmol) was added at 0° C. and the resultant mixture was stirred for 1 hour. After completion of the reaction, ethyl acetate was added to the reaction solution and the resultant mixture was washed with each of saturated ammonium chloride aqueous solution and saturated sodium chloride aqueous solution. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform) to obtain the title compound (1.64 g, yield 85%).

Workup

  1. additionwas added to the reaction solution
  2. washthe resultant mixture was washed with each of saturated ammonium chloride aqueous solution and saturated sodium chloride aqueous solution
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-d3a2d400781c4d889a38cf463dbb9f3d
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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