Hydrochloric Acid → HCID 23159882, compound

HRID 2110897Notes

Reaction equation

HRID 2110897 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Cl.Cl.[C:25]1([S:31]([CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>CN(C)C=O.O>[C:25]1([S:31]([CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][N:39]([CH2:2][C:3]3[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]4[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=4)=[CH:5][CH:4]=3)[CH2:38][CH2:37]2)(=[O:33])=[O:32])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 177498871-[2-(Benzenesulfonyl)ethyl]piperazine--hydrogen chloride (1/2)HCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoate

Product 1

HCID 23159882HCID 23159882, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-(4-([4-(chloromethyl)benzyl]oxy}phenyl)propanoate (50 mg, 0.16 mmol) in N,N-dimethylformamide (1 mL) were added a suspension of 1-(2-benzenesulfonylethyl)piperazine dihydrochloride (62 mg, 0.19 mmol) in N,N-dimethylformamide (0.5 mL) and potassium carbonate (80 mg, 0.58 mmol) and the mixture was stirred at 70° C. for 66 hr. Water (2 mL) was added to the reaction mixture, and the mixture was extracted with dichloromethane (2 mL). The organic layer was concentrated by a GeneVac centrifugation concentration apparatus under reduced pressure. The obtained product was dissolved in methanol (2 mL), 1 N aqueous sodium hydroxide solution (0.32 mL, 0.32 mmol) was added, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was acidified with 1 N Hydrochloric acid, and the precipitated crystals were collected by filtration, and washed with diethyl ether to give the title compound (51.5 mg, yield 63%). MS (ESI+, m/e) 523 (M+1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2 mL)
  2. concentrationThe organic layer was concentrated by a GeneVac centrifugation concentration apparatus under reduced pressure
  3. dissolutionThe obtained product was dissolved in methanol (2 mL)
  4. stirringthe mixture was stirred at room temperature for 18 hr
  5. filtrationthe precipitated crystals were collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-25d3e497b8b74f0fa3fc5b1d75fd575e
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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