Potassium Carbonate → HCID 86670984, compound

HRID 515356Notes

Reaction equation

HRID 515356 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[F:19][C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[N:29]([CH3:36])[CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:11][C:10]([F:13])([F:12])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:33]2[CH2:34][CH2:35][CH:30]([N:29]([C:21]3[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:20]=3[F:19])[CH3:36])[CH2:31][CH2:32]2)=[CH:4][CH:5]=1)([OH:18])[C:14]([F:17])([F:16])[F:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 67191568HCID 67191568, compound

Product 1

HCID 86670984HCID 86670984, compoundYield 124.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(4-(Bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (2.369 mmol, 1.141 mL, 798 mg), N-(2-fluoro-4-nitrophenyl)-N-methylpiperidin-4-amine (2.369 mmol, 600 mg) and potassium carbonate (7.11 mmol, 982 mg) were combined and stirred at 70° C. overnight in acetonitrile (50 mL). The reaction mixture was filtered and concentrated under vacuum. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulfate and concentrated under vacuum to give the intermediate 1,1,1,3,3,3-hexafluoro-2-(4-((4-((2-fluoro-4-nitrophenyl)(methyl)amino)piperidin-1-yl)methyl)phenyl)propan-2-ol (1.5 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-678adb4251a24733b505df7bf4ca6cb7
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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