Triethylamine → Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)piperazine-1-carboxylate

HRID 1352282Notes

Reaction equation

HRID 1352282 reaction equation
Br[C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.[N:8]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C>O1CCCC1>[C:17]([O:16][C:14]([N:8]1[CH2:13][CH2:12][N:11]([C:2]2[S:3][C:4]([Br:7])=[CH:5][N:6]=2)[CH2:10][CH2:9]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 3123942,5-Dibromothiazole

Product 1

HCID 34180719Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)piperazine-1-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 24.7 mmol 2,5-dibromothiazole, 49.4 mmol tert-butyl 1-piperazinecarboxylate and 74.1 mmol triethylamine in 24 ml tetrahydrofuran in a sealed tube was heated at 160° C. for 30 min under microwave irradiation. The reaction mixture was concentrated and the residue was purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as a white crystalline solid (yield 68%). MS (m/e): 350.2 ({81Br}M+H+, 100%), 348.2 ({79Br}M+H+, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (SiO2, ethyl acetate/heptane)

Sources & evidence

ORD record
ord-b956f16b8af04f8abf03a146fb4eeca9
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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