Bromine → HCID 67458099, compound

HRID 1028108Notes

Reaction equation

HRID 1028108 reaction equation
[Br:1]Br.[S:3]1[CH:7]=[CH:6][N:5]=[C:4]1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:7]1[S:3][C:4]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 60658779HCID 60658779, compound

Product 1

HCID 67458099HCID 67458099, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Bromine (0.14 mL, 2.7 mmol) was weighed into a vial and then diluted with acetic acid (1 mL). This solution was added dropwise (over 10 minutes) to a solution of ethyl 1-(1,3-thiazol-2-yl)piperidine-4-carboxylate (650 mg, 2.7 mmol) in acetic acid (12.5 mL). The mixture was then diluted with ethyl acetate (100 mL) and washed with water (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 840 mg (2.63 mmol, 97% yield) of ethyl 1-(5-bromo-1,3-thiazol-2-yl)piperidine-4-carboxylate as a green oil.

Workup

  1. washwashed with water (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b430eadc81f14116948713a96529db0e
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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