Methanol → 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl[1,4']bipiperidinyl-1'-carboxylate hydrochloride

HRID 2366411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366411
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[S:16][C:17]([N:20]3[CH2:25][CH2:24][CH:23](O)[CH2:22][CH2:21]3)=[CH:18][CH:19]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:32][CH2:31]1)=[O:29].C[OH:43]>N1C=CC=CC=1>[ClH:27].[C:12](/[C:11](/[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[CH:14]\[C:15]1[S:16][C:17]([N:20]2[CH2:25][CH2:24][CH:23]([CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][N:36]3[CH:33]3[CH2:34][CH2:35][N:30]([C:28]([OH:43])=[O:29])[CH2:31][CH2:32]3)[CH2:22][CH2:21]2)=[CH:18][CH:19]=1)#[N:13]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 98133754-Piperidinopiperidine-1-carbonyl chlorideHCID 16757522(Z)-2-(3,4-dimethoxyphenyl)-3-(5-(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrile

Produkt 1

HCID 672285281-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl[1,4']bipiperidinyl-1'-carboxylate hydrochlorideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Compound 6 (2.00 g) was dissolved in pyridine (50 mL), and 1-chlorocarbonyl-4-piperidinopiperidine (2.50 g) was added to the solution, followed by stirring under reflux for 2 hours. After completion of reaction, methanol was added to the reaction mixture, followed by stirring for 30 minutes. The solvent was evaporated under reduced pressure, and the residue was extracted with chloroform and purified water. The organic layer was dried over sodium sulfate anhydrate, and the solvent was evaporated to dryness. The residue was recrystallized from ethyl acetate, to thereby yield the target product (yield: 974 mg, 30%).

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. additionwas added to the reaction mixture
  3. stirringby stirring for 30 minutes
  4. customThe solvent was evaporated under reduced pressure
  5. extractionthe residue was extracted with chloroform
  6. custompurified water
  7. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  8. customthe solvent was evaporated to dryness
  9. customThe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-496751a46a364fe58662320598d58b09
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697742B2

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