Trifluoroacetic acid → HCID 23149850, compound

HRID 1670768Notes

Reaction equation

HRID 1670768 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:20][OH:21])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[Na+].[CH3:24]OS(=O)(=O)OC.[Cl-].[NH4+].FC(F)(F)C(O)=O.[OH-].[Na+]>O1CCCC1.C(Cl)Cl>[CH3:24][O:21][CH2:20][C:11]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 9994433Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate

Product 1

HCID 23149850HCID 23149850, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(Hydroxymethyl)-4-phenyl-1-piperidinecarboxylic acid tert-butyl ester (953 mg) was dissolved in tetrahydrofuran (10 ml), and the mixture was cooled to 0° C. Sodium hydride (157 mg) was added and the mixture was stirred for 20 min. Dimethylsulfuric acid (0.5 ml) was added, and the mixture was stirred for 5 hr. After completion of the reaction, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give a colorless oil. Methylene chloride (6 ml) and trifluoroacetic acid (0.5 ml) were added to the oil, and the mixture was stirred at room temperature for 7 hr. After completion of the reaction, 1N sodium hydroxide was added, and the mixture was extracted three times with chloroform. The organic layer was dried and the solvent was evaporated under reduced pressure to give 4-(methoxymethyl)-4-phenylpiperidine (237 mg, yield 35%).

Workup

  1. stirringthe mixture was stirred for 5 hr
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography
  7. customto give a colorless oil
  8. stirringthe mixture was stirred at room temperature for 7 hr
  9. additionwas added
  10. extractionthe mixture was extracted three times with chloroform
  11. customThe organic layer was dried
  12. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d304988800664edfba42df27a9d86cba
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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