Potassium Carbonate → HCID 86670981, compound

HRID 515352Notes

Reaction equation

HRID 515352 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.[CH3:19][N:20]([CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([N:20]([CH3:19])[CH:28]2[CH2:33][CH2:32][N:31]([CH2:2][C:3]3[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]=3)[CH2:30][CH2:29]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 67192413HCID 67192413, compound

Product 1

HCID 86670981HCID 86670981, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(4-(Bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.948 mmol, 0.657 g), N1-methyl-N1-(piperidin-4-yl)benzene-1,4-diamine (1.948 mmol, 0.4 g) and potassium carbonate (5.84 mmol, 0.808 g) were combined and stirred at room temperature for 1 hour 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 and concentrated under vacuum. The residue was purified by silica column chromatography (eluent: dichloromethane to 8% methanol in dichloromethane) to afford the title compound (260 mg). MS (ESI) m/z 462.4 [M+H]+

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. customdried
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica column chromatography (eluent: dichloromethane to 8% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3c2f224c33ba4eb5abbc8b2a8dcc8848
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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