Potassium Iodide → 6-[3-((R)-2-Methyl-pyrrolidin-1-yl)-propoxy]-3,4-dihydro-2H-naphthalen-1-one

HRID 2042631

Reaktionsgleichung

Reaktionsgleichung von HRID 2042631
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2.[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+].[I-].[K+]>C(#N)C>[CH3:17][C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 220232326-(3-Chloro-propoxy)-3,4-dihydro-2H-naphthalen-1-oneHCID 86646919(R)-2-methylpyrrolidine benzene sulfonate

Produkt 1

HCID 596519636-[3-((R)-2-Methyl-pyrrolidin-1-yl)-propoxy]-3,4-dihydro-2H-naphthalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a 1 L round bottom flask, 6-(3-chloro-propoxy)-3,4-dihydro-2H-naphthalen-1-one (10.0 g, 41.9 mmol), benzenesulfonate (R)-2-methyl-pyrrolidinium (13.15 g, 84.0 mmol), potassium carbonate (23.15 g, 168 mmol), and potassium iodide (100 mg, 0.6 mmol) in acetonitrile (600 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. Ethereal HCl was added and the solvents reduced under vacuum. Crystallization from MeOH/Et2O produced 8.75 g (65%). Mp 183-185° C. MS m/z=288 (M+H).

Aufarbeitung

  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. additionEthereal HCl was added
  10. customCrystallization from MeOH/Et2O
  11. customproduced 8.75 g (65%)

Quellen und Nachweise

ORD-Eintrag
ord-9087f63e8b9f4adc909a11bed7076e5d
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586588B2

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