1,2-Dichloroethane → 1-[(5-Hydroxy-2-pyridinyl)carbonyl]-piperidine

HRID 30458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30458
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[NH3:6].[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])=[N:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 2687405-Hydroxypyridine-2-carboxylic acid

Produkt 2

HCID 222AmmoniaAusbeute 5 %HCID 445154541-[(5-Hydroxy-2-pyridinyl)carbonyl]-piperidineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-hydroxy-2-pyridine carboxylic acid (2.00 g, 14.0 mmol) and piperidine (1.5 mL, 15 mmol) in DCM (150 mL) was added HOBt (2.80 g, 21.0 mmol), EDC (4.00 g, 21.0 mmol), and N-methyl morpholine (8.5 mL, 84 mmol). After 18 h the reaction mixture was concentrated. Chromatography of the residue (SiO2; 5-10% 2 M NH3 in MeOH/DCM) gave the title compound as a solid (1.30 g, 43%).

Aufarbeitung

  1. concentrationAfter 18 h the reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-985f1f5d40da4132a25e0a2f3b49fa42
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423147B2

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