tert-butyl 4-[(E)-2-(2-chloro-6-methylphenyl)vinyl]piperidine-1-carboxylate → 4-[(E)-2-(2-chloro-6-methylphenyl)vinyl]piperidine hydrochloride

HRID 1667316Notes

Reaction equation

HRID 1667316 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1/[CH:9]=[CH:10]/[CH:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1>C(O)C.Cl.C(O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1/[CH:9]=[CH:10]/[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 10088346tert-butyl 4-[(E)-2-(2-chloro-6-methylphenyl)vinyl]piperidine-1-carboxylate

Product 1

HCID 674436694-[(E)-2-(2-chloro-6-methylphenyl)vinyl]piperidine hydrochlorideYield 144.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21887872Ethanol hydrochlorideSolvent

Procedure

To a solution of 645 mg of tert-butyl 4-[(E)-2-(2-chloro-6-methylphenyl)vinyl]piperidine-1-carboxylate in 4 ml of ethanol, 3 ml of 35% hydrogen chloride-ethanol was added, followed by stirring at ambient temperature for 5 hours. The reaction mixture was evaporated under reduced pressure and the residue was azeotropically distilled with 5 ml of toluene 3 times to give crystals. The collected crystals were recrystallized from ethanol-ethyl acetate to give 377 mg of 4-[(E)-2-(2-chloro-6-methylphenyl)vinyl]piperidine hydrochloride.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. distillationthe residue was azeotropically distilled with 5 ml of toluene 3 times
  3. customto give crystals
  4. customThe collected crystals were recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-abf4fa44d5654b9f929efb49f9d3d6cf
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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