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

HRID 1436773Notes

Reaction equation

HRID 1436773 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-407f997a66d5400abbae550a001d8fa6
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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