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Chloroform → 2-Piperidineacetic acid ethyl ester hydrochloride

HRID 1645238
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1645238
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(Cl)(Cl)[Cl:14].C(Cl)Cl.CO>C(O)C.O=[Pt]=O>[ClH:14].[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6212Chloroform2×HCID 75960Ethyl 2-pyridylacetateHCID 21226129Dichloromethane methanol

Produkt 1

HCID 242012202-Piperidineacetic acid ethyl ester hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 702
Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Ethyl 2-(pyridin-2-yl)acetate (24.51 g, 148.4 mmol) was dissolved in ethanol (130 ml), and PtO2 (3.37 g, 14.84 mmol, 0.1 eq.) and chloroform (20 ml) were added. The suspension was stirred overnight under a H2 atmosphere (8 bar) at 40° C. According to TLC monitoring (silica gel, DCM/methanol 95:5), the reaction was incomplete, so that further chloroform (15 ml) was added and stirring was carried out for a further 2 d under a H2 atmosphere (8 bar) at 40° C. (TLC monitoring). After cooling, the catalyst was first removed by filtration over filtering earth and the filtrate was concentrated to dryness in vacuo. The ethyl 2-(piperidin-2-yl)acetate hydrochloride was used in the next stage without being purified further. Yield: 31.51 g, >100%

Aufarbeitung

  1. additionwas added
  2. stirringstirring
  3. waitwas carried out for a further 2 d under a H2 atmosphere
  4. customat 40° C.
  5. temperatureAfter cooling
  6. customthe catalyst was first removed by filtration
  7. filtrationover filtering earth
  8. concentrationthe filtrate was concentrated to dryness in vacuo
  9. customwithout being purified further

Quellen und Nachweise

ORD-Eintrag
ord-dcc53eb7a1924931a6ec925ac4f78bef
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08124624B2

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