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Diethyl Ether → Ethyl 1-carbamothioylpiperidine-4-carboxylate

HRID 1716502
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1716502
C1C2C(COC([N:18]=[C:19]=[S:20])=O)C3C(=CC=CC=3)C=2C=CC=1.[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])[CH3:22].C(OCC)C>C(Cl)(Cl)Cl>[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][N:29]([C:19](=[S:20])[NH2:18])[CH2:28][CH2:27]1)=[O:25])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 70770Ethyl 4-piperidinecarboxylateHCID 4154759Fmoc isothiocyanate

Produkt 1

HCID 23076419Ethyl 1-carbamothioylpiperidine-4-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

9-Fluorenylmethoxycarbonyl isothiocyanate (5.90 g, 21.0 mmol) was dissolved in chloroform (20 ml) and a chloroform (10 ml) solution of piperidine-4-carboxylic acid ethyl ester (3.30 g, 21.0 mmol) was added and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated in vacuo, and the residue obtained by adding diethyl ether was collected by filtration. This was dissolved in N,N-dimethylformamide (20 ml) and piperidine (20 ml) was added and the mixture was stirred at room temperature for 1 hour. After the reaction solution was washed with ethyl acetate and the organic layer was washed with a saturated bline and dried over sodium sulfate, the residue obtained by vacuum concentration was purified by silica gel chromatography (n-hexane:ethyl acetate), and the title compound (4.34 g, 100%) was obtained.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe residue obtained
  3. filtrationwas collected by filtration
  4. dissolutionThis was dissolved in N,N-dimethylformamide (20 ml)
  5. additionpiperidine (20 ml) was added
  6. stirringthe mixture was stirred at room temperature for 1 hour
  7. washAfter the reaction solution was washed with ethyl acetate
  8. washthe organic layer was washed with a saturated bline
  9. dry with materialdried over sodium sulfate
  10. customthe residue obtained by vacuum concentration
  11. customwas purified by silica gel chromatography (n-hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-73617e8d9c144308b825446b6c89e702
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07803801B2

Notizen zur Reaktion

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