Potassium Carbonate → HCID 86638558, compound

HRID 1807743Notes

Reaction equation

HRID 1807743 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 27342192-Methylpiperazine, (S)-HCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86638558HCID 86638558, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-Methylpiperazine (28 mmol, 2.8 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (28 mmol, 9.42 g) and potassium carbonate (55.9 mmol, 9.42 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 and 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 (4.55 g). MS (ESI) m/z 357.0 [M+H]+

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-56a8cf3e851b44c186d0acb2a3cc7cd0
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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