Potassium pyrosulfate → 1'-Benzyl-1',2',3',6'-tetrahydro-3,4'-bipyridine

HRID 1005208

Reaktionsgleichung

Reaktionsgleichung von HRID 1005208
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(OS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>C1C2C(CCCC2)CCC1.O>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 62681Potassium pyrosulfateHCID 10940791-Benzyl-4-(pyridin-3-YL)piperidin-4-OL

Produkt 1

HCID 221263831'-Benzyl-1',2',3',6'-tetrahydro-3,4'-bipyridineAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 7044DecalinLösungsmittel

Versuchsvorschrift

A dispersion of 4.52 g (16.8 mmol) of 1'-benzyl-2',3',5',6'-tetrahydro-1'H-[3,4']bipyridinyl-4'-ol and 18 g (71 mmol) of potassium disulphate in 35 ml of decalin was stirred at 190° C. for 30 minutes. After cooling to room temperature the reaction mixure was dissolved in water and extracted twice with 50 ml of toluene each time. Subsequently, the aqueous phase was made alkaline with sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate phase was thereafter dried over sodium sulphate and evaporated under reduced pressure. For purification, the crude product was chromatographed on silica gel using a 98:2:0.1 mixture of methylene chloride, methanol and ammonia as the eluent. There were obtained 4.03 g (61% of theory) of 1'-benzyl-1',2',3',6'-tetrahydro-3,4'-bipyridine as a yellowish oil; MS: 250 (M)+.

Aufarbeitung

  1. extractionextracted twice with 50 ml of toluene each time
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate phase was thereafter dried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customFor purification
  6. customthe crude product was chromatographed on silica gel using
  7. additiona 98:2:0.1 mixture of methylene chloride, methanol and ammonia as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-96ec8ca9c6bc4421be6ee1a9f27c6497
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06051712

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