Dimethyl Sulfoxide → Tert-butyl 4-(6-bromoquinolin-4-yl)piperazine-1-carboxylate

HRID 1792436Notes

Reaction equation

HRID 1792436 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[N:13]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C.CS(C)=O>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[N:16]1[CH2:15][CH2:14][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 22031412Tert-butyl 4-(6-bromoquinolin-4-yl)piperazine-1-carboxylateYield 71.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 243 mg 6-bromo-4-chloroquinoline, 373 mg t-butyl 1-piperazine carboxylate, 0.28 mL triethylamine and 10 mL dimethyl sulfoxide was stirred at 80° C. overnight. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed twice with water and then with brine and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 282 mg of the title compound as a pale yellow oil.

Workup

  1. customthe organic layer was separated
  2. washwashed twice with water
  3. dry with materialwith brine and dried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-27070b7657314989abb352220f1b84f4
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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