1-Acetylpiperazine → 1-[4-(2-Chloro-3-methyl-pyridin-4-ylmethyl)-piperazin-1-yl]-ethanone

HRID 1355523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1355523
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([CH2:9]Cl)[CH:5]=[CH:4][N:3]=1.[C:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:13])[CH3:12]>CS(C)=O>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([CH2:9][N:17]2[CH2:18][CH2:19][N:14]([C:11](=[O:13])[CH3:12])[CH2:15][CH2:16]2)[CH:5]=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 837951-AcetylpiperazineHCID 185068432-Chloro-4-(chloromethyl)-3-methylpyridine

Produkt 1

HCID 185068191-[4-(2-Chloro-3-methyl-pyridin-4-ylmethyl)-piperazin-1-yl]-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

(2-Chloro-3-methyl-pyridin-4-yl)-methanol (12-4, impure, 0.200 g) was dissolved in 5 mL anhydrous DCM under N2. Anhydrous DMF (0.098 mL, 1.3 mmol) and POCl3 (0.118 mL, 1.27 mmol) were added and the reaction was stirred at RT for 17 h. The reaction was quenched with sat NaHCO3 (aq) and extracted 3× with DCM. The organic phases were dried over Na2SO4, filtered and concentrated to provide 2-chloro-4-chloromethyl-3-methyl-pyridine still contaminated with a major by-product. 2-Chloro-4-chloromethyl-3-methyl-pyridine (impure, 0.215 g) was stirred in 3 mL DMSO. 1-Acetylpiperazine (0.626 g, 4.88 mmol was added and the reaction was stirred at RT overnight. The solution was purified by directly loading onto a preparative reverse phase column to afford an oil which slowly crystallizes. TFA salt: 1H NMR (CD3OD) δ 8.30 (d, 1H, J=5.0 Hz), 7.53 (d, 1H, J=5.0 Hz), 4.48 (s, 2H), 3.84 (bs, 4H), 3.39-3.30 (m, 4H), 2.14 (s, 3H).

Aufarbeitung

  1. customThe solution was purified
  2. customto afford an oil which
  3. customslowly crystallizes

Quellen und Nachweise

ORD-Eintrag
ord-b74347a309214c9885582d5c89e8df50
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586424B2

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