Ammonium Hydroxide → Ethyl 2-(piperidin-4-yl)-1,3-thiazole-5-carboxylate

HRID 715804

Reaction equation

HRID 715804 reaction equation
C(O[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])C.BrN1C(=O)CCC1=O.[C:19]([CH:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]1)(=[S:21])[NH2:20].[OH-].[NH4+]>O1CCOCC1.O>[NH:25]1[CH2:26][CH2:27][CH:22]([C:19]2[S:21][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:20]=2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 67184N-bromobutanimideHCID 221780Ethyl 3-ethoxy-2-propenoateHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

Product 1

HCID 86701983Ethyl 2-(piperidin-4-yl)-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
-10 °C

Procedure

Ethyl 3-ethoxyacrylate (1.50 g, 10.38 mml) was dissolved in dioxane/water and chilled to −10° C. N-Bromosuccinimide (2.03 g, 11.42 mmol) was added and the mixture was stirred 1 hour at room temperature. tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (2.54 g, 10.38 mmol) was added and the mixture was heated at 100° C. for 1 hour. The reaction mixture was poured into 25 mL saturated ammonium hydroxide and extracted with dichloromethane. The combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. Normal phase chromatography provided the title compound.

Workup

  1. temperaturethe mixture was heated at 100° C. for 1 hour
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-329f3457c78540efbaeee55cee310da5
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Linked notes

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