Ammonium Chloride → HCID 18182236, Verbindung

HRID 1359362

Reaktionsgleichung

Reaktionsgleichung von HRID 1359362
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:17]2[CH2:21][CH:20]=[CH:19][CH2:18]2)[N:12]=1.BrC1C=CC=C(N2CCCC2)N=1.[Cl-].[NH4+]>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].O1CCCC1>[CH2:1]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:17]2[CH2:21][CH:20]=[CH:19][CH2:18]2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 154702772-Bromo-6-(pyrrolidin-1-yl)pyridineHCID 18182355HCID 18182355, VerbindungHCID 178418336HCID 178418336, Verbindung

Produkt 1

HCID 18182236HCID 18182236, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

72.3 ml of a tetrahydrofuran solution containing 1.07 mol of benzylmagnesium chloride was added dropwise into a mixture of 11.6 g of a mixture of 2-bromo-6-(3-pyrroline-1-yl)pyridine and 2-bromo-6-(pyrrolidine-1-yl)pyridine and 20 ml of tetrahydrofuran containing 1.4 g of 1,3-bis(diphenylphosphino)propanenickel(II) chloride over 10 minutes in an ice bath. After cooling at room temperature overnight, the reaction solution was poured into aqueous saturated ammonium chloride and extracted with ethyl acetate. The organic phase was washed with aqueous saturated sodium chloride and the solvent was removed. The residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane and then with hexane/ethyl acetate (20:1), to give 11.8 g of the title compound as a mixture with 2-benzyl-6-(pyrrolidine-1-yl)pyridine.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with aqueous saturated sodium chloride
  3. customthe solvent was removed
  4. washeluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-17112d273d1749f8ab8152601b38eabf
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599917B1

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