Potassium Carbonate → 1-(4-Chlorobenzyl)-4-{[1-(4-fluorophenyl)piperidin-4-yl]amino}-1,3,5-triazin-2(1H)-one

HRID 1477708Notes

Reaction equation

HRID 1477708 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:4](=[O:16])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]2)=[CH:26][CH:25]=1>C(Cl)(Cl)Cl.O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:5]2[CH:6]=[N:7][C:2]([NH:36][CH:33]3[CH2:34][CH2:35][N:30]([C:27]4[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=4)[CH2:31][CH2:32]3)=[N:3][C:4]2=[O:16])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 196939451-(4-Fluorophenyl)piperidin-4-amineHCID 117839620HCID 117839620, compound

Product 1

HCID 1178399401-(4-Chlorobenzyl)-4-{[1-(4-fluorophenyl)piperidin-4-yl]amino}-1,3,5-triazin-2(1H)-oneYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a chloroform solution (1.1 mL) of 4-chloro-1-(4-chlorobenzyl)-1,3,5-triazin-2(1H)-one (59 mg, 0.23 mmol) synthesized in Reference Synthesis Example 11, potassium carbonate (80 mg, 0.58 mmol) and 1-(4-fluorophenyl)piperidine-4-amine (66 mg, 0.34 mmol) synthesized in Reference Synthesis Example 83 were added and the resultant mixture was stirred at room temperature for 30 minutes. After the completion of the reaction, water was added to the reaction solution and extraction with chloroform from the resultant reaction solution was performed. The organic layer was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/5→0/1 and next, ethyl acetate/methanol=19/1 (v/v)) to obtain the title compound (50 mg, yield: 52%).

Workup

  1. customsynthesized in Reference Synthesis Example 83
  2. additionwere added
  3. customreaction solution
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/5→0/1 and next, ethyl acetate/methanol=19/1 (v/v))

Sources & evidence

ORD record
ord-a2885db1740048438308962a4049e313
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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