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

HRID 1261653Notes

Reaction equation

HRID 1261653 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-1b4918ba3690449886c1af63127a8666
Source dataset
uspto-grants-2013_06
Patent number
US08470827B2

Reaction notes

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