1-Benzyloxycarbonyl-3-[2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidine → 3-[2-[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidine

HRID 602196Notes

Reaction equation

HRID 602196 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH:17]=[CH:18][C:19]2[S:23][C:22]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)=[N:21][C:20]=2[CH3:31])[CH2:12]1)=O)C1C=CC=CC=1>Cl>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]2[S:23][C:19]([CH:18]=[CH:17][CH:13]3[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]3)=[C:20]([CH3:31])[N:21]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 672674511-Benzyloxycarbonyl-3-[2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidine

Product 1

HCID 672670783-[2-[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidineYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-Benzyloxycarbonyl-3-[2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidine (1.16 g, 2.56 mmol) in 6 mol/L hydrochloric acid (25 mL) was stirred for 1 hour while being refluxed. Subsequently, the reaction mixture washed with ethyl acetate. A 10 mol/L aqueous sodium hydroxide solution was then added to make the mixture basic and the mixture was extracted with ethyl acetate. The extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. The residue was air-dried to give 749 mg (92%) of the desired compound as a yellow powder.

Workup

  1. temperaturewhile being refluxed
  2. washSubsequently, the reaction mixture washed with ethyl acetate
  3. additionA 10 mol/L aqueous sodium hydroxide solution was then added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract washed with brine
  6. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  7. customThe residue was air-dried

Sources & evidence

ORD record
ord-27b844eb270344d99ae76514f6bcf323
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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