Piperidine → (4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanone

HRID 551576

Reaktionsgleichung

Reaktionsgleichung von HRID 551576
CO[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:6][CH:5]=1.COC(=O)[C:21]1C=[CH:25][C:24]([CH:27]=O)=[N:23][CH:22]=1.[NH:30]1CCC[CH2:32][CH2:31]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.[OH-].[Na+]>[NH3:6].[CH:24]([N:23]1[CH2:22][CH2:21][N:30]([C:3]([C:4]2[CH:5]=[N:6][C:7]([CH2:10][N:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)=[CH:8][CH:9]=2)=[O:17])[CH2:31][CH2:32]1)([CH3:25])[CH3:27]

Komponenten

8

Edukt 4

HCID 8082PiperidineHCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 44515770Methyl 6-(piperidin-1-ylmethyl)nicotinate

Produkt 2

HCID 222AmmoniaAusbeute 1 %HCID 11522780(4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanoneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

6-Piperidin-1-ylmethyl-nicotinic acid methyl ester. To a solution of 6-formyl-nicotinic acid methyl ester (0.200 g, 1.21 mmol) and piperidine (0.14 mL, 1.33 mmol) in DCM (15 mL) was added NaB(OAc)3H (0.380 g, 1.80 mmol). After 18 h, the reaction was diluted with 1 N NaOH (10 mL) and extracted with DCM (2×50 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the residue (SiO2; 1-3% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.210 g, 74%).

Aufarbeitung

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2f926d3985e946eeba310fa414bb3afc
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947718B2

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