Potassium Carbonate → HCID 70873492, compound

HRID 2172206Notes

Reaction equation

HRID 2172206 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:32])([F:31])[O:9][C:10]1[CH:30]=[CH:29][C:13]([CH2:14][O:15][C:16]2[CH:28]=[CH:27][C:19]([CH2:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.Cl[C:34]1[S:35][C:36]2[CH:42]=[C:41]([OH:43])[CH:40]=[CH:39][C:37]=2[N:38]=1>CN(C)C=O>[F:32][C:8]([F:31])([F:7])[O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][O:15][C:16]2[CH:28]=[CH:27][C:19]([CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([C:34]4[S:35][C:36]5[CH:42]=[C:41]([OH:43])[CH:40]=[CH:39][C:37]=5[N:38]=4)[CH2:23][CH2:22]3)=[CH:18][CH:17]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 147498432-Chlorobenzo[d]thiazol-6-olHCID 70873441HCID 70873441, compound

Product 1

HCID 70873492HCID 70873492, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (1.02 g) and 4-[4-(4-trifluoromethoxybenzyloxy)benzyl]piperidine were added to an N,N-dimethylformamide solution (10 ml) of 2-chlorobenzothiazol-6-ol (1.37 g) and the mixture was stirred at 80° C. for 2 days. After being cooled to room temperature, the mixture was concentrated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1) to afford the title compound as a white powder (2.1 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1)

Sources & evidence

ORD record
ord-af87e31fed044901af5e4e05cf3a5df4
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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