Potassium Carbonate → HCID 86638559, compound

HRID 1807745Notes

Reaction equation

HRID 1807745 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH3:8][C@H:4]1[NH:3][C@@H:2]([CH3:1])[CH2:7][N:6]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([OH:26])([C:18]([F:19])([F:20])[F:21])[C:22]([F:23])([F:24])[F:25])=[CH:15][CH:16]=2)[CH2:5]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86638559HCID 86638559, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,6-cis-Dimethylpiperazine (40.3 mmol, 4.6 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (40.3 mmol, 13.58 g) and potassium carbonate (81 mmol, 11.13 g) were combined and stirred overnight at room temperature in acetonitrile (25 mL). The reaction mixture was diluted with ethyl acetate and filtered through dicalite. The filtrate was concentrated under vacuum. The resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 90/10/1 dichloromethane/methanol/ammonia) to afford the title compound (8.91 g).

Workup

  1. filtrationfiltered through dicalite
  2. concentrationThe filtrate was concentrated under vacuum
  3. customThe resulting residue was purified by silica chromatography (
  4. washeluting with a solvent gradient from dichloromethane to 90/10/1 dichloromethane/methanol/ammonia)

Sources & evidence

ORD record
ord-c272e6d662cf472a92b1cfc1080fa9ca
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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