Water → HCID 3732348, compound

HRID 1293113Notes

Reaction equation

HRID 1293113 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1.[OH-].[K+].O>CN(C)C=O.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][CH2:4][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 178418385HCID 178418385, compound

Product 1

HCID 3732348HCID 3732348, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,3-dibromopropane (510 μl, 5.0 mmol) in dimethylformamide (10 ml) was added benzotriazole (600 mg, 5.0 mmol) and KOH (430 mg, 7.7 mmol). After stirring for 20 h at room temp., water (15 ml) and ethyl acetate (15 ml) were added. The phases were separated and the aqueous phase was re-extracted with ethyl acetate (3×20 ml). The combined organic phases were dried over MgSO4 and concentrated, giving 1.44 g of the crude product. The crude product was purified by flash chromatography (0–10% methanol in DCM) yielding 705 mg (59%) of the title compound 64. TLC (5% methanol in DCM): Rf=0.4. HPLC-MS (Method A): M+=239.9 (UV/MS(%)=52/58).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was re-extracted with ethyl acetate (3×20 ml)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated
  5. customgiving 1.44 g of the crude product
  6. customThe crude product was purified by flash chromatography (0–10% methanol in DCM)

Sources & evidence

ORD record
ord-360f40b50ee3423892b09606ece8c382
Source dataset
uspto-grants-2007_07
Patent number
US07238713B2

Reaction notes

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