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

HRID 2043765Notes

Reaction equation

HRID 2043765 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(O)C>C(OCC)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 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2795532Ethyl 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)thiazole-4-carboxylate2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1,1-dimethylethyl 4-[4-(ethoxycarbonyl)-2-thiazolyl]-1-piperidine-carboxylate (11.1 g, 32.7 mmol) (i.e. the product of Example 1, Step A) in 100 mL of diethyl ether was treated with a solution of 2 M hydrogen chloride in diethyl ether (166 mL, 331 mmol) at 0° C. The resulting reaction precipitate was dissolved with 100 mL of absolute ethanol and was stirred overnight at room temperature. The reaction mixture was evaporated in vacuo, re-dissolved in ethanol and evaporated again to give 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.

Workup

  1. customThe resulting reaction precipitate
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionre-dissolved in ethanol
  4. customevaporated again
  5. customto give a solid
  6. waitThe resulting solid was placed under a high vacuum for several hours

Sources & evidence

ORD record
ord-d599dd226f5c44bea36941b19af7b023
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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