Potassium Carbonate → 1-{2-Methoxy-4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-ethanone

HRID 2042634Notes

Reaction equation

HRID 2042634 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[C:8]([O:15][CH3:16])[CH:7]=1.[CH3:17][C@@H:18]1[CH2:22][CH2:21][CH2:20][NH2+:19]1.C1(S([O-])(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[I-].[K+]>[CH3:16][O:15][C:8]1[CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:19]2[CH2:20][CH2:21][CH2:22][C@H:18]2[CH3:17])[CH:11]=[CH:10][C:9]=1[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 144071823-(p-Acetyl-m-methoxyphenoxy)propyl chlorideHCID 86646919(R)-2-methylpyrrolidine benzene sulfonate

Product 1

HCID 596519361-{2-Methoxy-4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-ethanoneYield 57.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a 250 mL round bottom flask, 1-[4-(3-chloro-propoxy)-2-methoxy-phenyl]-ethanone (6.18 g, 25.5 mmol), benzenesulfonate (R)-2-methyl-pyrrolidinium (12.4 g, 50.9 mmol), potassium carbonate (14.1 g, 102 mmol), and potassium iodide (20 mg, 0.12 mmol) in acetonitrile (100 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. The slurry was partitioned between methylene chloride and water, then washed with water three times. The organics were extracted three times with 3% citric acid solution. The combined aqueous layers were basified with sat. NaHCO3 sol. and extracted with methylene chloride, then dried over MgSO4. The solvents were removed under vacuum to produce 4.25 g (57%) of oil. MS m/z 292 (M+H).

Workup

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customThe slurry was partitioned between methylene chloride and water
  5. washwashed with water three times
  6. extractionThe organics were extracted three times with 3% citric acid solution
  7. extractionextracted with methylene chloride
  8. dry with materialdried over MgSO4
  9. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-3814c7b3d1e144608bd1a528c7a5ff4b
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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