4-Methylbenzyl chloride → 1-(4-Methylbenzyl)piperidin-4-ol

HRID 584718

Reaktionsgleichung

Reaktionsgleichung von HRID 584718
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C>[CH3:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 77224-Methylbenzyl chlorideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

Produkt 1

HCID 7914821-(4-Methylbenzyl)piperidin-4-olAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Synthesis of this compound was accomplished according to Scheme 33. To 5.05 g (50 mmol) of 4-hydroxypiperidine and 7.08 g (50 mmol) of p-methylbenzyl chloride in 25 mL of tert-butanol was added excess solid potassium carbonate, and the mixture was heated on a steam bath for 3 h. The mixture was cooled to room temperature and partitioned between ether and water. The organic phase was extracted with cold dilute HCl, and the acidic aqueous phase was extracted with ether twice. The aqueous phase was made basic with ice and 50% aqueous NaOH and extracted with ether. The ether phase was washed with dilute aqueous sodium bicarbonate solution, brine, dried, and evaporated under vacuum to give 5.3 g (52%) of 1-(4-methylbenzyl)-4-hydroxypiperidine (123) as an oil. GC/MS showed 100% purity with a molecular ion of 205.

Aufarbeitung

  1. customSynthesis of this compound
  2. temperaturethe mixture was heated on a steam bath for 3 h
  3. custompartitioned between ether and water
  4. extractionThe organic phase was extracted with cold dilute HCl
  5. extractionthe acidic aqueous phase was extracted with ether twice
  6. extractionextracted with ether
  7. washThe ether phase was washed with dilute aqueous sodium bicarbonate solution, brine
  8. customdried
  9. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-be1a1e9e8c574f94b5d0b79430183cfa
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927225B2

Verknüpfte Notizen

Wird geladen…