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Water → ethyl (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinate

HRID 59901
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 59901
C(N(CC)CC)C.[CH2:8]([O:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[O:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1)[CH3:9].Cl[C:25]1[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][N:26]=1.O>C(#N)C>[CH2:8]([O:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[O:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:25]2[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][N:26]=2)[CH2:15]1)[CH3:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 2799611Ethyl 6-chloronicotinateHCID 42553478(R)-3-(2-ethoxyphenoxy)piperidine

Produkt 1

HCID 131737070ethyl (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinateAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Triethylamine (8.1 mL, 80 mmol) was added to a stirred solution of (R)-3-(2-ethoxy-phenoxy)-piperidine (10 g, 39 mmol) and ethyl 6-chloronicotinate (7.2 ml, 39 mmol) in acetonitrile (100 mL) at 0° C. The reaction mixture was heated at 90° C. for 16 h. The mixture was cooled to ambient temperature, water (150 mL) was added, and the mixture was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed sequentially with water (100 mL) and brine (100 mL), then were dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography (13% ethyl acetate-hexanes) to afford ethyl (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinate (8.8 g). MS (ES+) 371.0 (M+H).

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionthe mixture was extracted with ethyl acetate (3×200 mL)
  3. washThe combined organic layers were washed sequentially with water (100 mL) and brine (100 mL)
  4. dry with materialwere dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography (13% ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-dcb5fc26fcd64ba39881d0c8a6b4c026
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440949B2

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