Hydrochloric Acid → 4-Piperidinemethanol, α-(trifluoromethyl)-, hydrochloride (1:1)

HRID 518716Notes

Reaction equation

HRID 518716 reaction equation
[F:1][C:2]([F:23])([F:22])[CH:3]([CH:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)[O:4][Si](C)(C)C.[ClH:24].CCOCC>C(Cl)Cl.CO>[ClH:24].[F:23][C:2]([F:1])([F:22])[CH:3]([CH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1)[OH:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 66728593HCID 66728593, compound

Product 1

HCID 667284574-Piperidinemethanol, α-(trifluoromethyl)-, hydrochloride (1:1)Yield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2,2,2-trifluoro-1-(trimethylsilyloxy)ethyl)piperidine-1-carboxylate (1.6 g, 4.50 mmol) in DCM (9 mL) and MeOH (1 mL) was added 2 M HCl in ether (11.25 mL, 22.51 mmol). The reaction was stirred at RT for 16 hours. The precipitate that formed was collected by vacuum filtration, washed with diethyl ether, and dried in vacuo to generate 2,2,2-trifluoro-1-(piperidin-4-yl)ethanol hydrochloride as a white powder (0.83 g, 84% yield).

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by vacuum filtration
  3. washwashed with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3e9fe27fbeb64672a506e9f4da0f6a78
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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