Hydrochloric Acid → HCID 44469961, compound

HRID 1091981Notes

Reaction equation

HRID 1091981 reaction equation
Cl.[F:2][C:3]([F:28])([O:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[CH:10][CH:9]=1)[CH:4]([F:6])[F:5]>O1CCOCC1>[F:28][C:3]([F:2])([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:26][CH:27]=1)[CH:4]([F:6])[F:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86624650HCID 86624650, compound

Product 1

HCID 44469961HCID 44469961, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl in dioxane (30 mL) was added to tert-butyl 4-[4-(1,1,2,2-tetrafluoroethoxy)phenoxy]piperidine-1-carboxylate (3.3 g). The mixture was stirred at ambient temperature for 30 minutes. The mixture was then concentrated at reduced pressure and triturated with diethyl ether. The resulting precipitate was filtered, washed with diethyl ether and dried under vacuum to give 4-[4-(1,1,2,2-tetrafluoroethoxy)phenoxy]piperidine as the hydrochloride salt (2.76 g); NMR Spectrum: (DMSOd6) 1.75-1.91 (m, 2H), 2.02-2.17 (m, 2H), 2.95-3.12 (m, 2H), 3.13-3.29 (m, 2H), 4.57-4.69 (m, 1H), 6.75 (tt, 1H), 7.06 (d, 2H), 7.19 (d, 2H), 8.95 (bs, 2H); Mass Spectrum: M+H+ 294.

Workup

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

Sources & evidence

ORD record
ord-f81ae5e5aec148b6b7c476c5887e791d
Source dataset
uspto-grants-2012_03
Patent number
US08129412B2

Reaction notes

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