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Acetic Acid → Benzyl 4-[4-[(3-chloropyrazin-2-yl)methylcarbamoyl]cyclohexyl]piperazine-1-carboxylate

HRID 245658
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 245658
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([CH:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1.C(O)(=O)C.[N:23]1([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C([BH3-])#N.[Na+]>ClCCl>[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([CH:12]2[CH2:17][CH2:16][CH:15]([N:26]3[CH2:25][CH2:24][N:23]([C:29]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])[CH2:28][CH2:27]3)[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 643495Benzyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 86674630N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide

Produkt 1

HCID 86674631Benzyl 4-[4-[(3-chloropyrazin-2-yl)methylcarbamoyl]cyclohexyl]piperazine-1-carboxylateAusbeute 134,6 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide (3.7 mmol, 1 g) was dissolved in dichloromethane (10 mL) and acetic acid (0.1 mL) was added. To this solution benzyl 1-piperazinecarboxylate (11.2 mmol, 2.16 mL) and sodium cyanoborohydride (7.47 mmol, 0.47 g) were added subsequently. The mixture was stirred overnight at room temperature. Reaction was quenched with an aqueous sodium hydrogencarbonate solution and extracted twice with dichloromethane. The combined organic layers were dried over phase separation filter, concentrated under reduced pressure and purified using column chromatography (silica gel; dichloromethane/methanol) to yield 2.35 g of the title compound as a mixture of cis and trans isomers which was used in the next step without further purification.

Aufarbeitung

  1. customReaction
  2. customwas quenched with an aqueous sodium hydrogencarbonate solution
  3. extractionextracted twice with dichloromethane
  4. customThe combined organic layers were dried over phase separation
  5. filtrationfilter
  6. concentrationconcentrated under reduced pressure
  7. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-610880f09088408884e26a553760192c
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658794B2

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