Water → HCID 68778443, compound

HRID 2263223Notes

Reaction equation

HRID 2263223 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11])=O.[NH2:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[S:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]1[N:12]=[C:13]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[S:14][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 27374492-Bromo-2'-fluoroacetophenone

Product 1

HCID 68778443HCID 68778443, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-1-(2-fluorophenyl)ethanone (977 mg, 4.50 mmol), tert-butyl 4-(aminocarbonothioyl)piperidine-1-carboxylate (1.0 g, 4.09 mmol) and potassium carbonate (1.13 g, 8.18 mmol) in dimethylformamide (30 ml) was stirred at 110° C. for 1 hour. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the desired product (391 mg, 26.3%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-f2fb521eb9624cd9916d81f666aae433
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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