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2-Methyltetrahydrofuran → 7-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2-yl dibenzylcarbamate

HRID 1518653
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1518653
[CH:1]1[CH:2]=[C:3]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]4[CH2:30][CH2:29][C:27](=[O:28])[NH:26][C:24]=4[CH:25]=3)[CH2:11][CH2:10]2)[C:4]([Cl:8])=[C:5]([Cl:7])[CH:6]=1.[CH2:31]([N:38]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:39](Cl)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC1CCCO1>C(OCC)(=O)C.O>[CH2:42]([N:38]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:39](=[O:40])[O:28][C:27]1[CH2:29][CH2:30][C:23]2[C:24](=[CH:25][C:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][N:9]([C:3]4[CH:2]=[CH:1][CH:6]=[C:5]([Cl:7])[C:4]=4[Cl:8])[CH2:10][CH2:11]3)=[CH:21][CH:22]=2)[N:26]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 73012-MethyltetrahydrofuranHCID 60795AripiprazoleHCID 12712012Carbamic chloride, bis(phenylmethyl)-

Produkt 1

HCID 565969567-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2-yl dibenzylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

A mixture of aripiprazole (1.5 g, 3.3 mmol), dibenzylcarbamoyl chloride (1.74 g, 6.7 mmol) silver carbonate (3.75 g, 13.4 mmol) and 2-methyltetrahydrofuran (30 mL) was heated at reflux for 4 days. The reaction mixture was cooled, diluted with ethyl acetate and water, and then filtered through celite. The organic phase was separated, dried over MgSO4 and evaporated. The residue obtained was further purified on silica eluting with ethyl acetate/tetrahydrofuran to give after evaporation of the major product containing fractions, Compound-80 (1.02 g) was a yellow oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 days
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through celite
  5. customThe organic phase was separated
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue obtained
  9. customwas further purified on silica eluting with ethyl acetate/tetrahydrofuran
  10. customto give
  11. customafter evaporation of the major product
  12. additioncontaining fractions, Compound-80 (1.02 g)

Quellen und Nachweise

ORD-Eintrag
ord-218fe1e14185492984f2870112c42049
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09072788B2

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