Water → HCID 57890406, compound

HRID 1819999Notes

Reaction equation

HRID 1819999 reaction equation
BrC1C=CC(C([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:21][CH2:20][CH2:19][N:18]3[CH3:22])=[CH:13][CH:12]=2)=O)=CC=1.O>Cl>[CH3:22][N:18]1[CH2:19][CH2:20][CH2:21][CH:17]1[C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][NH2:8])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 962WaterHCID 23090900HCID 23090900, compound

Product 1

HCID 57890406HCID 57890406, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-bromo-N-{2-[4-(1-methyl-2-pyrrolidinyl)phenyl]ethyl}benzamide (1.12 g, 2.89 mmol) obtained in Example 136 in concentrated hydrochloric acid (14 ml) was stirred at 100° C. for one day. Water was added to the reaction mixture, and the mixture was washed with diethyl ether and basified with potassium carbonate. This was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate:methanol=1:1) to give the title compound (305 mg).

Workup

  1. washthe mixture was washed with diethyl ether
  2. extractionThis was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate:methanol=1:1)

Sources & evidence

ORD record
ord-3b2e15f0b38a45f5aae91608b01d6427
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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