Hydrochloric Acid → 1,1-Dimethylethyl 4-[5-(methoxycarbonyl)-2-thiazolyl]-1-piperazinecarboxylate

HRID 2043719Notes

Reaction equation

HRID 2043719 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:15]1[S:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:19]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.Cl>CS(C)=O.[I-].[K+].O>[CH3:23][O:22][C:20]([C:17]1[S:16][C:15]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[N:19][CH:18]=1)=[O:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2773502Methyl 2-bromothiazole-5-carboxylateHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 600321491,1-Dimethylethyl 4-[5-(methoxycarbonyl)-2-thiazolyl]-1-piperazinecarboxylateYield 88.9%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

1,1-Dimethylethyl 1-piperazinecarboxylate (1.86 g, 10 mmol), methyl 2-bromo-5-thiazolecarboxylate (2.0 g, 9.0 mmol), diazabicycloundecene (1.5 mL, 10 mmol) and a catalytic amount of potassium iodide (2 mg) were dissolved in 10 mL of dry dimethylsulfoxide and stirred at ambient temperature for 1 h to give a precipitate. An additional 10 mL of dimethylsulfoxide was added, the mixture was heated briefly to dissolve the solids, and the mixture was stirred at ambient temperature for 40 minutes and then at 50° C. for 2 h. The warm solution was added dropwise with stirring to 200 mL of cold water containing 10 mL of 1 N aqueous hydrochloric acid, and the resulting precipitate was filtered, dissolved in ether, dried over MgSO4 and concentrated under reduced pressure to give 2.62 g of the title compound as a light yellow solid.

Workup

  1. customto give a precipitate
  2. temperaturethe mixture was heated briefly
  3. dissolutionto dissolve the solids
  4. stirringthe mixture was stirred at ambient temperature for 40 minutes
  5. waitat 50° C. for 2 h
  6. additionThe warm solution was added dropwise
  7. filtrationthe resulting precipitate was filtered
  8. dissolutiondissolved in ether
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4f4387d9dd14776b7cdd4d44b3451a5
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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