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Trifluoroacetic acid → (R)-3-(2-ethoxyphenoxy)piperidine

HRID 59885
Notes
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Reaction equation

HRID 59885 reaction equation
[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]1)[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131737068tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylate

Product 1

HCID 42553478(R)-3-(2-ethoxyphenoxy)piperidineYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

To a solution of tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylate (73 g, 227 mmol) in CH2Cl2 (300 mL) at 20-25° C. was added trifluoroacetic acid (150 mL). The reaction mixture was allowed to stir at 20-25° C. for 4 hours. The mixture was concentrated under reduced pressure, and the residue was dissolved in H2O (200 mL) and basified with saturated NaHCO3 solution (200 mL). The mixture was extracted with EtOAc (3 times with 200 mL). The organic extracts were dried over Na2SO4 and concentrated to afford (R)-3-(2-ethoxyphenoxy)piperidine (45 g, 89%). MS (ES+) 222.2 (M+H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in H2O (200 mL)
  3. extractionThe mixture was extracted with EtOAc (3 times with 200 mL)
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1725428ea045439f82dc57456ad64915
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440949B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes