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Triethylamine → HCID 59752974, Verbindung

HRID 1909687
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1909687
Cl.[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH2:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.Br[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].C(N(CC)CC)C>ClCCl.O>[CH3:31][O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C@H:14]1[CH2:13][O:12][C:11]1[CH:20]=[CH:21][C:8]([O:7][C:6]2[CH:22]=[CH:23][C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 107604Methyl 4-bromobutyrateHCID 68996119HCID 68996119, Verbindung

Produkt 1

HCID 59752974HCID 59752974, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of (S)-2-[4-(4-chloro-phenoxy)-phenoxymethyl]-piperidine hydrochloride (218 mg, 0.615 mmol), methyl 4-bromobutyrate (139 mg, 0.769 mmol), and triethylamine (124 mg, 1.23 mmol) in dichloromethane (2.5 mL) was heated for 18 h at 30° C. The mixture was diluted with 5 mls of water and extracted with dichloromethane (8 mL). The aqueous layer was re-extracted with ethyl acetate (8 mL). The combined organic layers were dried over anhy. Na2SO4 and the solvent was removed in vacuo to obtain the crude mixture, which was purified by silica gel flash chromatography to obtain the title product (87 mg, 34%): 1H NMR (400 MHz, CDCl3) δ 1.52-1.86 (m, 6H), 2.11-2.12 (m, 1H), 2.21-2.2 (m, 1H), 2.27-2.33 (m, 3H), 2.49-2.56 (m, 1H), 2.66-2.70 (m, 1H), 2.74-2.81 (m, 1H), 2.86-2.91 (m, 1H) 3.64 (s, 3H), 3.91-3.94 (dd, 1H J1=4.4 Hz, J2=10 Hz), 4.0-4.03 (dd, 1H J1=4.4 Hz, J2=10 Hz) 6.86-6.89 (m, 4H), 6.94-6.96 (m, 2H), 7.23-7.25 (m, 2H); MS

Aufarbeitung

  1. extractionextracted with dichloromethane (8 mL)
  2. extractionThe aqueous layer was re-extracted with ethyl acetate (8 mL)
  3. customThe combined organic layers were dried over anhy
  4. customNa2SO4 and the solvent was removed in vacuo
  5. customto obtain the crude mixture, which
  6. customwas purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5ea32473d1df4dc7b06eebee827a6ac6
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08598359B2

Notizen zur Reaktion

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