Potassium Carbonate → HCID 86638557, compound

HRID 1807741Notes

Reaction equation

HRID 1807741 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:25])([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[F:18][C:17]([F:19])([F:20])[C:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:6]2[CH2:5][CH2:4][NH:3][C@H:2]([CH3:1])[CH2:7]2)=[CH:11][CH:12]=1)([OH:25])[C:21]([F:22])([F:24])[F:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 73304342-Methylpiperazine, (R)-HCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86638557HCID 86638557, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-2-Methylpiperazine (37.9 mmol, 3.8 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (37.9 mmol, 12.79 g) and potassium carbonate (76 mmol, 10.49 g) were stirred at room temperature in acetonitrile (50 mL) overnight. 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 85/15/1.5 dichloromethane/methanol/ammonia) to afford the title compound (4.06 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 85/15/1.5 dichloromethane/methanol/ammonia)

Sources & evidence

ORD record
ord-9ca3467a27fa41db920811859863c823
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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