5-Phenyl-2-furaldehyde → 3-(3-((5-Phenylfuran-2-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine dihydrochloride

HRID 1678321

Reaktionsgleichung

Reaktionsgleichung von HRID 1678321
[Cl-:1].[NH3+:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[NH+:11][CH:12]=[CH:13][CH:14]=1)=O.[Cl-].[C:16]1([C:22]2[O:26][C:25]([CH:27]=O)=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(C)C>[ClH:1].[ClH:1].[C:16]1([C:22]2[O:26][C:25]([CH:27]=[C:6]3[CH2:5][CH2:4][CH2:3][N:2]=[C:7]3[C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 27694205-Phenyl-2-furaldehydeHCID 673376573-(5-Ammoniopentanoyl)pyridinium chloride

Produkt 1

HCID 673394513-(3-((5-Phenylfuran-2-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine dihydrochlorideAusbeute 181,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

3-(5-Ammoniopentanoyl)pyridinium chloride (188 mg, 0.75 mmol) was transferred to a reaction vessel and treated with isopropanol (12 mL). 5-Phenyl-2-furaldehyde (193 mg, 1.12 mmol) was added, the reaction vessel was sealed, and the reaction was heated to 85° C. with stirring for 6 hours. The reaction was then cooled to room temperature, and the precipitate was recovered by vacuum filtration, washed with isopropanol and ether then dried under vacuum giving 264 mg (91%) of an orange solid. LC-MS: RT=5.15 min, [M+H]+=315.1.

Aufarbeitung

  1. customthe reaction vessel was sealed
  2. temperatureThe reaction was then cooled to room temperature
  3. filtrationthe precipitate was recovered by vacuum filtration
  4. washwashed with isopropanol and ether
  5. customthen dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-75ab2f627f15424ab020297c32ceee07
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008499B2

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