Hydrogen chloride-ethyl acetate → 4-({4-[(3-Fluorobenzyl)oxy]phenyl}sulfanyl)piperidine

HRID 2074231Notes

Reaction equation

HRID 2074231 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:9][CH:8]=1.Cl.CCOC(C)=O>CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([S:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57507753HCID 57507753, compound

Product 1

HCID 574217934-({4-[(3-Fluorobenzyl)oxy]phenyl}sulfanyl)piperidineYield 86.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl 4-({4-[(3-fluorobenzyl)oxy]phenyl}sulfanyl)piperidine-1-carboxylate (501 mg) was dissolved in EtOAc (5 ml), and a 4 M hydrogen chloride/EtOAc solution (3 ml) was added thereto, followed by stirring at room temperature for 3 hours. Then, the solvent was evaporated under reduced pressure. The residue was dissolved in water, neutralized with an aqueous 1 M sodium hydroxide solution, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 4-({4-[(3-fluorobenzyl)oxy]phenyl}sulfanyl)piperidine (328 mg).

Workup

  1. customThen, the solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ed5179b1068840c48684d8fbea78f00f
Source dataset
uspto-grants-2011_04
Patent number
US07919494B2

Reaction notes

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