Hydrochloric Acid → 4-[4-(2,2,2-Trifluoroethoxy)phenoxy]piperidine

HRID 1091978Notes

Reaction equation

HRID 1091978 reaction equation
[F:1][C:2]([F:26])([F:25])[CH2:3][O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[CH:7][CH:6]=1.Cl>O1CCOCC1>[F:26][C:2]([F:1])([F:25])[CH2:3][O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66593153Tert-butyl 4-[4-(2,2,2-trifluoroethoxy)phenoxy]piperidine-1-carboxylate

Product 1

HCID 665930264-[4-(2,2,2-Trifluoroethoxy)phenoxy]piperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 4-[4-(2,2,2-trifluoroethoxy)phenoxy]piperidine-1-carboxylate (3 g) was added 4 molar hydrogen chloride in 1,4-dioxane (50 ml), stirred at ambient temperature for 1 hour. The solvent was removed and the resultant solid triturated and washed twice with a small amount of diethyl ether to yield 4-[4-(2,2,2-trifluoroethoxy)phenoxy]piperidine as a hydrochloride salt (2.4 g). NMR Spectrum: (DMSOd6) 1.7 (m, 2H), 2.0 (m, 2H), 3.0 (m, 2H), 3.2 (m, 2H), 4.5 (m, 1H), 4.6 (m, 2H), 6.9 (m, 4H), 8.8 (broad, 2H). Mass Spectrum: M−H− 276.

Workup

  1. customThe solvent was removed
  2. customthe resultant solid triturated
  3. washwashed twice with a small amount of diethyl ether

Sources & evidence

ORD record
ord-7ada577a404d4fc0be3d1f44b8bdcc50
Source dataset
uspto-grants-2012_03
Patent number
US08129412B2

Reaction notes

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