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Water → 3-Carbomethoxy-1,3-dibenzyl-4-piperidone

HRID 1042320
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1042320
Cl.[CH3:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)=[O:5].[H-].[Na+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH3:2][O:3][C:4]([C:6]1([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11](=[O:12])[CH2:10][CH2:9][N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 107479Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride

Produkt 1

HCID 542328573-Carbomethoxy-1,3-dibenzyl-4-piperidoneAusbeute 114,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Benzyl-4-oxo-piperidine-3-carboxylic acid methyl ester hydrochloride salt (1, Z=benzyl) (15 g, 52.9 mmol) was suspended in DMF (150 mL) and cooled to 0° C. Sodium hydride (4.23 g, 105.8 mmol) was added portionwise over 1 h and the contents were allowed to warm to ambient temperature and stir for a further 1 h. Benzyl bromide (6.3 mL, 53.0 mmol) was added over 15 min and the contents were stirred for a further 68 h at ambient temperature. 10 mL of water were added and the contents were diluted with 400 mL of ethyl acetate, washed with water (200 mL), saturated sodium bicarbonate (200 mL) and brine (200 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to give 20.5 g yellow oil that was purified by flash column chromatography (3:2 cyclohexane/CH2Cl2 to 100% CH2Cl2) to give 17.52 g (98%) of the title compound as a colorless oil. LC-MS: RT=2.80 min. (M+H)+ 338, (M-OMe)+ 306.

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. stirringthe contents were stirred for a further 68 h at ambient temperature
  3. washwashed with water (200 mL), saturated sodium bicarbonate (200 mL) and brine (200 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e2878feaee4243c88932cadb1b334a92
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08557839B2

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