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Hydrochloric Acid → Ethyl 4-(4-phenylbenzoyl)-1-piperidinecarboxylate

HRID 2305258
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2305258
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:18]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1)=[O:19].Cl>ClCCCl>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:18]([CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]3)=[O:19])=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7095BiphenylHCID 6451240Aluminum(III) ChlorideHCID 11096122Ethyl 4-(chlorocarbonyl)-1-piperidinecarboxylate

Produkt 1

HCID 18432031Ethyl 4-(4-phenylbenzoyl)-1-piperidinecarboxylateAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11
1,2-Dichloroethane
Lösungsmittel
2×

Versuchsvorschrift

A mixture of 1,1′-biphenyl (0.3 mol) and aluminum-(III)-chloride (0.6 mol) in 1,2-dichloroethane (500 ml) was stirred. A mixture of ethyl 4-(chlorocarbonyl)-1-piperidinecarboxylate (0.3 mol) in 1,2-dichloroethane (100 ml) was added dropwise over a 30-minutes period (exothermic temperature rise to 30° C.). The mixture was stirred at room temperature for 90 minutes, poured out into ice and HCl and extracted with DCM. CH3OH was added. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 42 g of ethyl 4-(4-phenylbenzoyl)-1-piperidinecarboxylate (interm. 9).

Aufarbeitung

  1. additionwas added dropwise over a 30-minutes period (exothermic temperature rise to 30° C.)
  2. stirringThe mixture was stirred at room temperature for 90 minutes
  3. extractionextracted with DCM
  4. additionCH3OH was added
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from DIPE
  13. filtrationThe precipitate was filtered off
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8549dca7edad4184ace96501ca84df33
Quelldatensatz
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06440440B1

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