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Water → benzyl 2'-oxo-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]-1-carboxylate

HRID 1695911
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1695911
ClC1N=C(Cl)N=C(Cl)N=1.O[N:11]=[C:12]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:14]2([CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH2:15]2)[CH2:13]1.[OH2:36]>CN(C=O)C>[O:36]=[C:12]1[CH2:13][C:14]2([CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:18][CH2:19]2)[C:30]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:11]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 72297710Benzyl 3-(hydroxyimino)-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

Produkt 1

HCID 59433237benzyl 2'-oxo-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]-1-carboxylateAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2,4,6-trichloro-[1,3,5]-triazine (1.32 g, 7.16 mmol) was added to DMF (9.6 mL) maintained at 25° C. The reaction was monitored by TLC until TCT was consumed. Then benzyl 3-(hydroxyimino)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (1.6 g, 4.77 mmol) in DMF (17 mL) was added. After the addition, the mixture was stirred at room temperature overnight. Water was added. The mixture was extracted with EtOAc. The combined organic layers were washed with sat. Na2CO3, followed by 1N HCl and brine, dried over Na2SO4 and concentrated. The residue was purified by prep HPLC to obtain benzyl 2′-oxo-2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline]-1-carboxylate (260 mg, yield 16%).

Aufarbeitung

  1. customwas consumed
  2. additionAfter the addition
  3. extractionThe mixture was extracted with EtOAc
  4. washThe combined organic layers were washed with sat. Na2CO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-27cd934a0a964a6a9e54a6ab2dbb7467
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163737B2

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