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