Piperidin-4-ol → HCID 117839477, compound

HRID 1477681Notes

Reaction equation

HRID 1477681 reaction equation
[CH3:1][C:2]1[N:7]([CH2:8][C:9]2[S:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)[C:6](=[O:18])[N:5]=[C:4](SC)[N:3]=1.[NH:21]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]1>O1CCOCC1>[OH:27][CH:24]1[CH2:25][CH2:26][N:21]([C:4]2[N:3]=[C:2]([CH3:1])[N:7]([CH2:8][C:9]3[S:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=3)[C:6](=[O:18])[N:5]=2)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 117839530HCID 117839530, compound

Product 1

HCID 117839477HCID 117839477, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 1,4-dioxane solution (1.0 mL) of 6-methyl-4-(methylthio)-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (321 mg, 1.00 mmol) synthesized in Reference Synthesis Example 292, 4-piperidinol (202 mg, 2.00 mmol) was added and the resultant mixture was stirred under reflux by heating for 10 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0→10/1) to obtain the title compound (374 mg, yield 100%).

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. temperatureby heating for 10 hours
  4. customAfter completion of the reaction
  5. concentrationthe reaction solution was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0→10/1)

Sources & evidence

ORD record
ord-b52da9a35cbd46f590c1da68623a8410
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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