Dimethylformamide → HCID 765041, Verbindung

HRID 1291167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291167
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])C.CN(C)[CH:21]=[O:22]>>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:14]2[CH2:15][CH2:16][CH:21]([OH:22])[CH2:18][CH2:17]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromide

Produkt 1

HCID 765041HCID 765041, Verbindung

Versuchsvorschrift

1.0 g (0.00989 mol) of 4-hydroxypiperidi,ne was dissolved in 50 ml of dimethylformamide and cooled to 0°. 2.56g (0.001186 mol) of 4-nitro-benzyl bromide and 2.78 ml (0.0198 mol) of triethylamine were added and the mixture was left to come to room temperature. It was stirred for 16 hrs., the solvent was distilled off and the residue was taken up in dichloromethane. The organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated and the residue was chromatographed on silica gel with dichloromethane/methanol (9:1) as the eluent. 0.836 g (36%) of 1-(4-nitro-benzyl-piperidin-4-ol was obtained as beige crystals; m.p. 114°-115°.

Aufarbeitung

  1. temperaturecooled to 0°
  2. waitthe mixture was left
  3. customto come to room temperature
  4. distillation, the solvent was distilled off
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customthe residue was chromatographed on silica gel with dichloromethane/methanol (9:1) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-6f2fe62fa2a94975b3b7cdb543531a8a
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753679

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