Water → 2-(1-(4-Fluorobenzyl)piperidin-4-yl)ethan-1-ol

HRID 54547

Reaktionsgleichung

Reaktionsgleichung von HRID 54547
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:7]2[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]2)=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 680234-FluorobenzaldehydeHCID 739534-Piperidineethanol

Produkt 1

HCID 105618622-(1-(4-Fluorobenzyl)piperidin-4-yl)ethan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

A mixture of 4-(2-hydroxyethyl)piperidine (21.5 g), 4-fluorobenzaldehyde (17.5 ml) and p-toluene sulfonic acid (3 mg) in benzene (200 ml) was refluxed with separating water as the benzene azeotrope. After 2 hours, the mixture was evaporated in vacuo. The residue was dissolved in methanol (200 ml) and sodium borohydride (6.3 g) was added thereto at 5° C. After stirring at ambient temperature for 1 hour, the mixture was evaporated in vacuo. 4N Hydrochloric acid (200 ml) was added to the residue and washed with ethyl acetate. The aqueous layer was made basic to pH 10 with potassium carbonate and extracted with ethyl acetate. The extract was washed with water and brine, and dried over magnesium sulfate, and evaporated in vacuo to give 1-(4-fluorobenzyl)-4-(2-hydroxyethyl)piperidine (32.0 g) as an oil.

Aufarbeitung

  1. customthe mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in methanol (200 ml)
  3. additionsodium borohydride (6.3 g) was added
  4. customat 5° C
  5. customthe mixture was evaporated in vacuo
  6. addition4N Hydrochloric acid (200 ml) was added to the residue
  7. washwashed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water and brine
  10. dry with materialdried over magnesium sulfate
  11. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-81c94a8cf3a54d16a3ac4f055b91e857
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622976

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