Hydrochloric Acid → 4-[4-(3,3,3-Trifluoropropoxy)phenoxy]piperidine

HRID 1091987Notes

Reaction equation

HRID 1091987 reaction equation
Cl.[F:2][C:3]([F:28])([F:27])[CH2:4][CH2:5][O:6][C:7]1[CH:26]=[CH:25][C:10]([O:11][CH:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)=[CH:9][CH:8]=1>O1CCOCC1>[F:28][C:3]([F:2])([F:27])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66592935Tert-butyl 4-[4-(3,3,3-trifluoropropoxy)phenoxy]piperidine-1-carboxylate

Product 1

HCID 665928524-[4-(3,3,3-Trifluoropropoxy)phenoxy]piperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl in dioxane (10 mL) was added to tert-butyl 4-[4-(3,3,3-trifluoropropoxy)phenoxy]piperidine-1-carboxylate (550 mg). The mixture was stirred at ambient temperature for 10 minutes. The mixture was then concentrated at reduced pressure and triturated with diethyl ether and stirred for 10 minutes. The resulting precipitate was filtered and dried under vacuum to give 4-[4-(3,3,3-trifluoropropoxy)phenoxy]piperidine as the hydrochloride salt (286 mg); NMR Spectrum: (DMSOd6) 1.76-1.88 (m, 2H), 2.01-2.12 (m, 2H), 2.66-2.82 (m, 2H), 2.97-3.10 (m, 2H), 3.14-3.27 (m, 2H), 4.15 (t, 2H), 4.46-4.56 (m, 1H), 6.87-6.98 (m, 4H), 9.03 (bs, 2H); Mass Spectrum: M+H+ 290.

Workup

  1. concentrationThe mixture was then concentrated at reduced pressure
  2. customtriturated with diethyl ether
  3. stirringstirred for 10 minutes
  4. filtrationThe resulting precipitate was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c9b4d3c471c74fdcbeb6f636c35d0439
Source dataset
uspto-grants-2012_03
Patent number
US08129412B2

Reaction notes

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