Hydrochloric Acid → 3-[1-(3-Fluorophenyl)methylidene]piperidine hydrochloride

HRID 928079Notes

Reaction equation

HRID 928079 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]2[CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]2)[CH:6]=[CH:7][CH:8]=1>O1CCOCC1.CCOCC>[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86713375Tert-butyl 3-[1-(3-fluorophenyl)methylidene]piperidine-1-carboxylate2×

Product 1

HCID 709838913-[1-(3-Fluorophenyl)methylidene]piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of HCl in dioxane (4M, 30 mL) was added to a solution of tert-butyl 3-[1-(3-fluorophenyl)methylidene]piperidine-1-carboxylate (Intermediate 227, 2.38 g) in ether (30 mL) and the mixture was stirred at room temperature for 5 hours. The mixture was concentrated in vacuo and the residue was treated with ether. The solid was collected by filtration, washed with ether and dried under vacuum to give 3-[1-(3-fluorophenyl)methylidene]piperidine hydrochloride (1.64 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was treated with ether
  3. filtrationThe solid was collected by filtration
  4. washwashed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1444adab56f54a87a3b0ccc60405ac1f
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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