Dimethylformamide → 2-[3,5-Dimethyl-4-(6-trifluoromethylbenzothiazole-2-yl)piperazine-1-yl]ethanol

HRID 420576Notes

Reaction equation

HRID 420576 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH:4]([CH3:8])[N:3]1[C:9]1[S:10][C:11]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.Br[CH2:23][CH2:24][O:25][Si](C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:8][CH:4]1[N:3]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:2]([CH3:1])[CH2:7][N:6]([CH2:23][CH2:24][OH:25])[CH2:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 66657765HCID 66657765, compound

Product 1

HCID 666578182-[3,5-Dimethyl-4-(6-trifluoromethylbenzothiazole-2-yl)piperazine-1-yl]ethanolYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(2,6-dimethyl piperazine-1-yl)-6-trifluoromethyl benzothiazole (360 mg), (2-bromoethoxy)-t-butyldimethyl silane (257 uL), potassium carbonate (157 mg) and dimethylformamide (2 mL) was stirred at 60° C. for 20 hours. To the reaction solution was added water and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium carbonate. After evaporating the solvent, the residue was purified by column chromatograph on silica gel to give the title compound (265 mg). Yield: 65%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium carbonate
  4. customAfter evaporating the solvent
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-5a2630c67f7e47619126cd3cda469e24
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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