Hydrochloric Acid → 1-Benzyl-4-[4-(2-hydroxy-ethyl)-phenyl]-piperidin-4-ol

HRID 1005007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1005007
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][O:23]C3CCCCO3)=[CH:17][CH:16]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][OH:23])=[CH:19][CH:20]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22127334(RS)-1-benzyl-4-[4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl]-piperidin-4-ol

Produkt 1

HCID 149034381-Benzyl-4-[4-(2-hydroxy-ethyl)-phenyl]-piperidin-4-olAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 78 g (197 mmol) of (RS)-1-benzyl-4-[4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl]-piperidin-4-ol in 400 ml of methanol was treated with 470 ml of 2N hydrochloric acid and stirred at room temperature for 5 hours. For the working-up, the reaction solution was poured into 1500 ml of saturated sodium hydrogen carbonate solution and subsequently extracted three times with 1000 ml of ethyl acetate each time. The combined organic phases were dried over sodium sulphate and evaporated under reduced pressure. For purification of the crude substance, a flash chromatography on silica gel using a 95:5 mixture of methylene chloride and methanol as the eluent was carried out. There were obtained 51.6 g (84% of theory) of 1-benzyl-4-[4-(2-hydroxy-ethyl)-phenyl]-piperidin-4-ol as a yellowish solid; MS: 312 (M+H)+.

Aufarbeitung

  1. extractionsubsequently extracted three times with 1000 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customFor purification of the crude substance
  5. additiona flash chromatography on silica gel using a 95:5 mixture of methylene chloride and methanol as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-1c6212361cc54554a6ef5ac2b612937a
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06051712

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