Benzyl Alcohol → 1-(Pyridin-4-yl)piperidine-4-carbamic acid benzyl ester

HRID 412622

Reaktionsgleichung

Reaktionsgleichung von HRID 412622
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10](C(O)=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C)C=O>[CH2:40]([O:47][C:21](=[O:30])[NH:18][CH:10]1[CH2:9][CH2:8][N:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH2:12][CH2:11]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acid

Produkt 1

HCID 600641081-(Pyridin-4-yl)piperidine-4-carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 1-(pyridin-4-yl)piperidine-4-carboxylic acid (11.18 g) and triethylamine (11.3 ml) in dimethylformamide (110 ml) was added diphenylphosphoryl azide (12.9 ml) at room temperature, and the mixture was stirred at 80° C. for 30 min. Benzyl alcohol (6.17 ml) was added at the same temperature, and the mixture was stirred for 12 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=99:1-95:5) and dried under reduced pressure to give the title compound (9.46 g).

Aufarbeitung

  1. stirringthe mixture was stirred for 12 hours
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=99:1-95:5)
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-82a0b3d961e04a4680847d4b53b7ebcd
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562828B1

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