Cesium carbonate → HCID 70873513, compound

HRID 2172226Notes

Reaction equation

HRID 2172226 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:35]1[CH:40]=[CH:39][C:38]([O:41][C:42]([F:45])([F:44])[F:43])=[CH:37][CH:36]=1.C(CC(=O)C(C)(C)C)(=O)C(C)(C)C.[Cl-].[NH4+]>[Cu](Cl)Cl.CN1CCCC1=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][C:35]4[CH:36]=[CH:37][C:38]([O:41][C:42]([F:43])([F:44])[F:45])=[CH:39][CH:40]=4)=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 70873672HCID 70873672, compound

Product 1

HCID 70873513HCID 70873513, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

4-({1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenyl]piperidin-4-yl}methyl)phenol (1.10 g, 3.0 mmol), cesium carbonate (0.977 g, 3.0 mmol), N-methylpyrrolidinone (5 ml), 1-bromo-4-(trifluoromethoxy)benzene (0.723 g, 2.99 mmol) and dipivaloylmethane (0.3 g, 1.5 mmol) were mixed, and the atmosphere was replaced with nitrogen. Copper chloride (0.030 g, 0.3 mmol) was added thereto and stirred at 120° C. for 24 hours. An ammonium chloride aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25) to afford the title compound as a colorless powder (0.84 g, 53%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25)

Sources & evidence

ORD record
ord-491710ff6cde4c6c8d1782953e2ca561
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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