Hydrochloric Acid → 4-(4-Ethenyl-2-thiazolyl)piperidine

HRID 1528522Notes

Reaction equation

HRID 1528522 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[S:6][CH:7]=1)=[CH2:2].Cl.C(OCC)C.[OH-].[Na+]>ClCCl>[CH:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[S:6][CH:7]=1)=[CH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 687436451,1-Dimethylethyl 4-(4-ethenyl-2-thiazolyl)-1-piperidinecarboxylate2×

Product 1

HCID 687444094-(4-Ethenyl-2-thiazolyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-(4-ethenyl-2-thiazolyl)-1-piperidinecarboxylate (i.e. the product of Example 4, Step A) (471 mg, 1.6 mmol) in dichloromethane (5 mL) was added a solution of hydrogen chloride in diethyl ether (2.0 M, 7 mL, 14 mmol). The reaction mixture was stirred under nitrogen at room temperature for 4 h, and then 1 N aqueous sodium hydroxide solution was added until pH of the reaction mixture increased to about 10. The resulting mixture was extracted with dichloromethane (2×). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give 302 mg of the title compound as an oil.

Workup

  1. temperatureincreased to about 10
  2. extractionThe resulting mixture was extracted with dichloromethane (2×)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-def331b273f941dab75c8a51c1c19fde
Source dataset
uspto-grants-2015_07
Patent number
US09090604B2

Reaction notes

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