1-Chloroethyl chloroformate → 5-methyl-3H-spiro[1-benzofuran-2,4'-piperidine]

HRID 270039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270039
C([N:8]1[CH2:13][CH2:12][C:11]2([CH2:17][C:16]3[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCl>[CH3:22][C:19]1[CH:20]=[CH:21][C:15]2[O:14][C:11]3([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:17][C:16]=2[CH:18]=1

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 598336331'-benzyl-5-methyl-3H-spiro[1-benzofuran-2,4'-piperidine]

Produkt 1

HCID 598336485-methyl-3H-spiro[1-benzofuran-2,4'-piperidine]Ausbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1′-benzyl-5-methyl-3H-spiro[1-benzofuran-2,4′-piperidine](0.12 g, 0.41 mol) in dichloromethane (3 ml) was added 1-chloroethyl chloroformate (87 mg, 0.61 mmol). The solution was stirred at room temperature overnight. The solvent was removed i. vacuo. The residue was dissolved in methanol (3 ml), and the solution was heated at 70° C. for 2 h. The solvent was eeporated, and the residue treated with diethyl ether. The precipitate formed was collected by filtration, washed with diethyl ether, and dissolved in methanol (1 ml). Water (25 ml) was added, and pH was adjusted to 10 by addition of 2 M aq. NaOH. The mixture was extracted with dichloromethane (2×25 ml), and the combined organic extracts were dried over Na2SO4. Evaporation of solvent afforded brownish oil (64 mg, 77%).

Aufarbeitung

  1. customThe solvent was removed i
  2. dissolutionThe residue was dissolved in methanol (3 ml)
  3. temperaturethe solution was heated at 70° C. for 2 h
  4. additionthe residue treated with diethyl ether
  5. customThe precipitate formed
  6. filtrationwas collected by filtration
  7. washwashed with diethyl ether
  8. dissolutiondissolved in methanol (1 ml)
  9. additionWater (25 ml) was added
  10. additionpH was adjusted to 10 by addition of 2 M aq. NaOH
  11. extractionThe mixture was extracted with dichloromethane (2×25 ml)
  12. dry with materialthe combined organic extracts were dried over Na2SO4
  13. customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-dcf8e072bc964a3cace2094380090ae6
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449475B2

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