tert-Butyl 4-hydroxy-4-[2-(trifluoromethyl)phenyl]piperidine-1-carboxylate → 4-[2-(Trifluoromethyl)phenyl]piperidin-4-ol

HRID 1044575Notes

Reaction equation

HRID 1044575 reaction equation
[OH:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1>Cl.CCOCC>[F:24][C:21]([F:22])([F:23])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:2]1([OH:1])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 49760255tert-Butyl 4-hydroxy-4-[2-(trifluoromethyl)phenyl]piperidine-1-carboxylate

Product 1

HCID 226370654-[2-(Trifluoromethyl)phenyl]piperidin-4-olYield 69.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

tert-Butyl 4-hydroxy-4-[2-(trifluoromethyl)phenyl]piperidine-1-carboxylate (0.40 g, 1.0 mmol) was dissolved in a 2.0 M solution of HCl in ether (5 mL). After being stirred at room temperature overnight, the solution was diluted with ether. The white solid was filtered and washed with ether to give 170 mg of pure product. MS calculated for C12H14F3NO: (M+H) 246; found 246.1.

Workup

  1. filtrationThe white solid was filtered
  2. washwashed with ether

Sources & evidence

ORD record
ord-249b360e20434ab4812c443d0659c7f9
Source dataset
uspto-grants-2013_10
Patent number
US08563582B2

Reaction notes

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