Potassium Carbonate → HCID 67974924, compound

HRID 468804Notes

Reaction equation

HRID 468804 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[Cl:13].[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[CH2:2][N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 22027761Methyl 4-(bromomethyl)-3-chlorobenzoate

Product 1

HCID 67974924HCID 67974924, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-(bromomethyl)-3-chlorobenzoate (400 mg, 1.5 mmol), 1-methylpiperazine (100 mg, 1.0 mmol), and potassium carbonate (276 mg, 2.0 mmol) in N,N-dimethylformamide (2.5 mL) were stirred at room temperature overnight. The mixture was concentrated and diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried and concentrated to give product (270 mg, 58%). LCMS (ESI): RT (min)=0.934, M+H+=282.8, method=B.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. customThe combined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5a0abbde06cf411cb13890727326868d
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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