Hydrochloric Acid → N-(1,3-thiazol-2-yl)piperidin-4-amine

HRID 1880646Notes

Reaction equation

HRID 1880646 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>ClCCCl>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 231309421,1-Dimethylethyl 4-(2-thiazolylamino)-1-piperidinecarboxylate

Product 1

HCID 43345808N-(1,3-thiazol-2-yl)piperidin-4-amineYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

810 mg (2.85 mmol) tert-butyl-4-(thiazol-2-ylamino)piperidine-1-carboxylate was dissolved in DCE (10 ml) and an ethereal HCl soln (10 ml) was added. After 3 h of stirring at RT, the solvent was removed in vacuo. The residue was taken up by water and adjusted to a pH of 11 with a 10% aq. NaOH soln. Extraction then took place with chloroform. The organic phase was washed with water and sat. aq. NaCl soln, dried over MgSO4 and filtered, and the solvent was removed in vacuo. 483 mg (2.64 mmol, 93%) N-(piperidin-4-yl)thiazol-2-amine was thus obtained.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionExtraction
  3. washThe organic phase was washed with water and sat. aq. NaCl soln
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-42e4cc1f4b03427bae0521705d8aca52
Source dataset
uspto-grants-2012_11
Patent number
US08318774B2

Reaction notes

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