3-(4-Chlorophenoxy)benzaldehyde → 3-(3-(3-(4-Chlorophenoxy)benzylidene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine dihydrochloride

HRID 1444745

Reaktionsgleichung

Reaktionsgleichung von HRID 1444745
[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-].[Cl:16][C:17]1[CH:31]=[CH:30][C:20]([O:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH:25]=O)=[CH:19][CH:18]=1>C(O)(C)C>[ClH:16].[ClH:1].[Cl:16][C:17]1[CH:31]=[CH:30][C:20]([O:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH:25]=[C:6]2[CH2:5][CH2:4][CH2:3][N:2]=[C:7]2[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 6160153-(4-Chlorophenoxy)benzaldehydeHCID 673376573-(5-Ammoniopentanoyl)pyridinium chloride

Produkt 1

HCID 673369523-(3-(3-(4-Chlorophenoxy)benzylidene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine dihydrochlorideAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-(5-Ammoniopentanoyl)pyridinium chloride (162 mg, 0.64 mmol) was suspended in a reaction vessel with i-propanol (12 mL). 3-(4-chlorophenoxy)benzaldehyde (225 mg, 0.97 mmol) was then added and the reaction vessel sealed. The reaction was heated to 80° C. overnight and then cooled to room temperature. The precipitate was recovered by vacuum filtration, washed with a 20% i-propanol in hexane solution then dried under vacuum giving 161 mg (56%) of a tan-colored solid. LC-MS: RT=6.22 min, [M+H]+=375.1.

Aufarbeitung

  1. customthe reaction vessel sealed
  2. temperaturecooled to room temperature
  3. filtrationThe precipitate was recovered by vacuum filtration
  4. washwashed with a 20% i-propanol in hexane solution
  5. customthen dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-edab8f3343634601be0527e713a2acbf
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662965B2

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