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Iodoethane → ethyl 6-{[(3R)-1-benzyl-3-piperidinyl]amino}-5-chloronicotinate

HRID 226465
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 226465
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].I[CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+].Cl.Cl.[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([NH2:36])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([NH:36][C:3]2[C:2]([Cl:1])=[CH:10][C:6]([C:7]([O:9][CH2:13][CH3:14])=[O:8])=[CH:5][N:4]=2)[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 11430Potassium Carbonate2×HCID 2479875,6-Dichloronicotinic acidHCID 22831369(R)-1-benzyl-3-Aminopiperidine Dihydrochloride

Produkt 1

HCID 68964359ethyl 6-{[(3R)-1-benzyl-3-piperidinyl]amino}-5-chloronicotinateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of 5,6-dichloronicotinic acid (7.0, 35 mmol) in DMF were added iodoethane (6.0 g, 38.5 mmol) and K2CO3 (5.8 g, 42 mmol) at ambient temperature and the mixture was stirred at 45° C. for 5 hrs. To the reaction mixture were added (3R)-1-benzyl-3-piperidinamine dihydrochloride (10.1 g, 38.5 mmol) and K2CO3 (16.9 g, 122 mmol) and the reaction mixture was stirred at 90° C. for 18 hrs. The reaction mixture was evaporated in vacuo and the residue was partitioned between water and EtOAc. The organic layer was separated, washed water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (EtOAc-hexane/1-4˜1-3) to give ethyl 6-{[(3R)-1-benzyl-3-piperidinyl]amino}-5-chloronicotinate (6.75 g, 52%) as a powder.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 90° C. for 18 hrs
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. customThe organic layer was separated
  5. washwashed water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (EtOAc-hexane/1-4˜1-3)

Quellen und Nachweise

ORD-Eintrag
ord-9ab467195a50421283683d60a06869e0
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07557127B2

Notizen zur Reaktion

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