Pyrrolidine → 1-[(4-Bromophenoxy)acetyl]pyrrolidine

HRID 1257837Notes

Reaction equation

HRID 1257837 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([OH:16])=O)=[CH:10][CH:9]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl.CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:16])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 74657p-Bromophenoxyacetic acid

Product 1

HCID 7876791-[(4-Bromophenoxy)acetyl]pyrrolidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.5 mL, 5.9 mmol) was added to a suspension of (4-bromophenoxy)acetic acid (0.462 g, 2.0 mmol) in methylene chloride (10 mL) and 2 drops of N,N-dimethylformamide. The mixture was stirred at RT for 2 h. The solvent was evaporated under reduced pressure. The residue was diluted with methylene chloride (10 mL), cooled with ice-water bath, and 1M of sodium hydroxide aqueous solution (3.0 mL) was added. To the mixture was added pyrrolidine (167 μL, 2.0 mmol). The mixture was stirred and allowed to warm to RT. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was directly used in next step without further purification (550 mg, 96.7%). LCMS: (M+H)=286.0/284.0

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with methylene chloride (10 mL)
  3. temperaturecooled with ice-water bath
  4. addition1M of sodium hydroxide aqueous solution (3.0 mL) was added
  5. stirringThe mixture was stirred
  6. temperatureto warm to RT
  7. customThe organic layer was separated
  8. washwashed with water and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was directly used in next step without further purification (550 mg, 96.7%)

Sources & evidence

ORD record
ord-55f70253dee94a0a979e4ad18792b519
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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