Triethylamine → 2-(4-Fluorophenoxy)-1-(3-phenylpyrrolidin-1-yl)ethanone

HRID 1404447Notes

Reaction equation

HRID 1404447 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:12][C:13]1[CH:23]=[CH:22][C:16]([O:17][CH2:18][C:19](Cl)=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[F:12][C:13]1[CH:23]=[CH:22][C:16]([O:17][CH2:18][C:19]([N:9]2[CH2:10][CH2:11][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8]2)=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2759057(4-Fluorophenoxy)acetyl chlorideHCID 31467433-Phenylpyrrolidine

Product 1

HCID 29278932-(4-Fluorophenoxy)-1-(3-phenylpyrrolidin-1-yl)ethanoneYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-phenylpyrrolidine (294 mg, 2 mmol) in dry dichloromethane (6 mL) is cooled in an ice bath, and (4-fluoro-phenoxy)-acetyl chloride (471.5 mg, 2.5 mmol, 1.25 eq) and triethylamine (417 μL, 3 mmol, 1.5 eq) are added. After stirring for 6 hours at room temperature the reaction mixture is diluted with dichloromethane (10 mL). The organic solution is subsequently washed with 1 M KHSO4, 5% NaHCO3 and brine. After drying over Na2SO4, dichloromethane is removed in vacuo and the crude material is purified by flash chromatography (silicagel, ethyl acetate/toluene 1:4). The fractions containing 2-(4-fluorophenoxy)-1-(3-phenylpyrrolidin-1-yl)ethan-1-one are collected and the solvent is removed in vacuo to give 495 mg of colorless oil.

Workup

  1. washThe organic solution is subsequently washed with 1 M KHSO4, 5% NaHCO3 and brine
  2. dry with materialAfter drying over Na2SO4, dichloromethane
  3. customis removed in vacuo
  4. customthe crude material is purified by flash chromatography (silicagel, ethyl acetate/toluene 1:4)
  5. additionThe fractions containing 2-(4-fluorophenoxy)-1-(3-phenylpyrrolidin-1-yl)ethan-1-one
  6. customare collected
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-489236a76b854f4b82142f7c9377b575
Source dataset
uspto-grants-2014_12
Patent number
US08912329B2

Reaction notes

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