Sulfuric Acid → HCID 23149943, compound

HRID 238272Notes

Reaction equation

HRID 238272 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])(O)[CH2:10][CH2:9]1)=O)(C)(C)C.S(=O)(=O)(O)O.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 49760229tert-Butyl 4-(2,4-difluorophenyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 23149943HCID 23149943, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(2,4-Difluoro-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.4 g) was dissolved in toluene (10 mL). Concentrated sulphuric acid (0.3 mL) was added and the mixture was heated at reflux for 2 hours and then allowed to stand at room temperature overnight. A solution of aqueous sodium hydroxide (1 N, 30 mL) was added and the products extracted into ethyl acetate. The organic solution was dried with magnesium sulphate, filtered and the solvent removed by evaporation under vacuum to give the title compound as a dark oil (0.2 g) which was used without further purification. LCMS m/z 196.1 [M+H]+. R.T.=2.12 min (Analytical Method 4).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. extractionthe products extracted into ethyl acetate
  4. dry with materialThe organic solution was dried with magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-a12ae00f53b8499dbc78f8a8d8154f3d
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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