1-Isopropylpiperazine → HCID 86700444, compound

HRID 879633Notes

Reaction equation

HRID 879633 reaction equation
Br[C:2]1[S:6][CH:5]=[N:4][CH:3]=1.[CH:7]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([CH3:9])[CH3:8]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[OH-].[K+].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1(C)C=CC=CC=1>[CH:7]([N:10]1[CH2:15][CH2:14][N:13]([C:2]2[S:6][CH:5]=[N:4][CH:3]=2)[CH2:12][CH2:11]1)([CH3:9])[CH3:8]

Participants

7

Reactant 2

HCID 780131-IsopropylpiperazineHCID 5460595-Bromothiazole

Product 1

HCID 86700444HCID 86700444, compound

Reagents, catalysts & solvents 4

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 14797Potassium HydroxideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a 5 mL microwave reaction tube containing 5-bromothiazole (359 mg, 2.19 mmol), isopropylpiperazine (330 mg, 1.1 eq.), Bis(tri-t-butylphosphine)palladium (0) (22 mg, 15 mol %), cetyltrimethylammonium bromide (15 mg, 30 mol %), toluene (3 mL) was added one drop of 50% KOH aqueous solution. The reaction was heated to 110° C. for 4 hours. The reaction was cooled down and extracted using ethyl acetate/brine. The organic layers were concentrated and purified via Combiflash (0-20% MeOH/Ethyl acetate) to give desired product. LCMS-ESI+: calc'd for C10H18N3S: 212.1 (M+H+); Found: 212.1 (M+H+).

Workup

  1. temperatureThe reaction was cooled down
  2. extractionextracted
  3. concentrationThe organic layers were concentrated
  4. custompurified via Combiflash (0-20% MeOH/Ethyl acetate)

Sources & evidence

ORD record
ord-96e111aea11140ce87befcfed4097000
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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