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Potassium Carbonate → ethyl 4-[3-[4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenoxy]propyl]-1-piperidinecarboxylate

HRID 1030906
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1030906
Cl.[O:2]1[CH2:7][CH2:6][CH2:5][N:4]=[C:3]1[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]1>CN(C)C=O>[O:2]1[CH2:7][CH2:6][CH2:5][N:4]=[C:3]1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:22][CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]2)=[CH:10][CH:9]=1
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 14989201Ethyl 4-(3-chloropropyl)-1-piperidinecarboxylateHCID 1364045384-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol hydrochloride

Produkt 1

HCID 14989203ethyl 4-[3-[4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenoxy]propyl]-1-piperidinecarboxylateAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 15 parts of 4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol hydrochloride, 29 parts of potassium carbonate and 180 parts of N,N-dimethylformamide was stirred for 1 hour at about 80° C. Then there were added 16.4 parts of ethyl 4-(3-chloropropyl)-1-piperidinecarboxylate and stirring was continued overnight at about 95° C. The reaction mixture was poured into ice water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 18.8 parts (71.7%) of ethyl 4-[3-[4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenoxy]propyl]-1-piperidinecarboxylate; mp. 128.5° C. (int. 59).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued overnight at about 95° C
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c36a8691f6404a01b0cbfc73e18beca3
Quelldatensatz
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05106973

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