Hydrochloric Acid → HCID 21604779, compound

HRID 2255517Notes

Reaction equation

HRID 2255517 reaction equation
Br[C:2]1[C:3]([O:21][CH3:22])=[C:4]([C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)[C:5]([NH:7][CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[CH2:14][CH3:15])=[O:6].Cl.[OH-:24].[K+]>CS(C)=O.O>[CH2:14]([N:10]1[CH2:11][CH2:12][CH2:13][C@H:9]1[CH2:8][NH:7][C:5](=[O:6])[C:4]1[C:3]([O:21][CH3:22])=[C:2]([OH:24])[CH:18]=[CH:17][C:16]=1[O:19][CH3:20])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54477Remoxipride

Product 1

HCID 21604779HCID 21604779, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent3×

Procedure

(S)-(-)-3-Bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,6-dimethoxybenzamide ×HCl×H2O (1.0 g, 0.0026 mol) was dissolved in 25 ml dimethylsulphoxide. A suspension of crushed potassium hydroxide (1.0 g, 0.018 mol) in 5 ml water was added and the mixture was heated at reflux for 2 h. After cooling 200 ml of water was added and the reaction mixture was neutralized and extracted with chloroform. Drying and evaporation of the solvent gave a residue containing a mixture of several products including the starting material. Separation on silica column with CH2Cl2 -C2H5OH-NH3 (90:9:1) gave 0.05 g of the title compound as a oil.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 h
  4. additionwas added
  5. extractionextracted with chloroform
  6. customDrying
  7. customevaporation of the solvent
  8. customgave a residue
  9. additioncontaining
  10. additiona mixture of several products
  11. customSeparation on silica column with CH2Cl2 -C2H5OH-NH3 (90:9:1)

Sources & evidence

ORD record
ord-6dd77c71ec864c05bec6851c99228b6c
Source dataset
uspto-grants-1993_08
Patent number
US05240957

Reaction notes

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