Hydrochloric Acid → Ethyl 2-(4-piperidinyl)-4-thiazolecarboxylate monohydrochloride

HRID 660040Notes

Reaction equation

HRID 660040 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])[CH3:2].[ClH:24]>C(OCC)C.C(O)C>[ClH:24].[NH:14]1[CH2:15][CH2:16][CH:11]([C:8]2[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 2795532Ethyl 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)thiazole-4-carboxylate2×

Product 1

HCID 66956430Ethyl 2-(4-piperidinyl)-4-thiazolecarboxylate monohydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1,1-dimethylethyl 4-[4-(ethoxycarbonyl)-2-thiazolyl]-1-piperidinecarboxylate (11.1 g, 32.7 mmol) (i.e. the product of Example 1, Step A) in diethyl ether (100 mL) at 0° C. was treated with a solution of hydrogen chloride in diethyl ether (2 M, 166 mL, 331 mmol). The reaction mixture then was diluted with absolute ethanol (100 mL) and stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, re-dissolved in ethanol and evaporated again to leave a solid. The resulting solid was placed under a high vacuum for several hours to give 10.38 g of the title compound as a hygroscopic white powder. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionre-dissolved in ethanol
  3. customevaporated again
  4. customto leave a solid
  5. waitThe resulting solid was placed under a high vacuum for several hours

Sources & evidence

ORD record
ord-925052cd6cf24be08892666d26e70175
Source dataset
uspto-grants-2011_12
Patent number
US08084468B2

Reaction notes

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