Benzoyl chloride → HCID 21074604, compound

HRID 1373686Notes

Reaction equation

HRID 1373686 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([CH:6]=CC2C=CC(OC)=C(OC)C=2)[NH:2]1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[C:19]1([C:18]([N:1]2[CH2:5][CH2:4][CH:3]([NH2:2])[CH2:6]2)=[O:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 69424807HCID 69424807, compound

Product 1

HCID 21074604HCID 21074604, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-aza-2-pyrrolidin-3-ylvinyl)-1,2-dimethoxybenzene (3 mmol) and benzoyl chloride (3.5 mmol), a compound of formula (10), were added to a mixture of dry methylene chloride (15 mL) and sodium carbonate (600 mg). The mixture was stirred for hours and then filtered through a Celite™ bed. Solvent was removed from the filtrate by evaporation, and the residue was dissolved in a mixture of methanesulfonic acid (3.84 g) in 20 mL tetrahydrofuran:water (3:1), and stirred for 60 hours. The solution was neutralized with sodium carbonate, filtered, and solvent removed from the filtrate under reduced pressure. The residue was purified on a silica gel flash chromatography column, to obtain 3-aminopyrrolidinyl phenyl ketone as an oil.

Workup

  1. filtrationfiltered through a Celite™ bed
  2. customSolvent was removed from the filtrate by evaporation
  3. dissolutionthe residue was dissolved in a mixture of methanesulfonic acid (3.84 g) in 20 mL tetrahydrofuran:water (3:1)
  4. stirringstirred for 60 hours
  5. filtrationfiltered
  6. customsolvent removed from the filtrate under reduced pressure
  7. customThe residue was purified on a silica gel flash chromatography column

Sources & evidence

ORD record
ord-fcd06a552705498f92e21e3cb6fbad41
Source dataset
uspto-grants-2007_01
Patent number
US07163928B2

Reaction notes

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