Sodium Hydroxide → 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl alcohol

HRID 267071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 267071
C([O:4][CH2:5][CH2:6][CH:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:37])[CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]([OH:36])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:9][C:8]1([CH3:39])[CH3:38])(=O)C.[OH-].[Na+]>CO>[OH:36][C:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][C:13]([C:10]2[CH:11]=[CH:12][CH:7]([CH2:6][CH2:5][OH:4])[C:8]([CH3:39])([CH3:38])[CH:9]=2)=[O:37])[CH2:18][CH2:19]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 229063064-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl acetate

Produkt 1

HCID 701480474-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
68 °C

Versuchsvorschrift

Dissolve 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl acetate (69.0 g, 0.131 mol) in methanol (2.5 L) and add 10% aqueous sodium hydroxide (769 mL, 1.92 mol). Stir at reflux for 1.5 hours, cool to 68° C. and evaporate the solvent in vacuo to a residue (700 mL). Add chloroform (1 L) and stir until solids are dissolved. Separate the organic phase and extract the aqueous phase with chloroform (3×300 mL). Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo and recrystallize (toluene) to give the title compound as a cream-colored powder; mp 135°-137° C.

Aufarbeitung

  1. temperatureat reflux for 1.5 hours
  2. customevaporate the solvent in vacuo to a residue (700 mL)
  3. stirringAdd chloroform (1 L) and stir until solids
  4. dissolutionare dissolved
  5. customSeparate the organic phase
  6. extractionextract the aqueous phase with chloroform (3×300 mL)
  7. dry with materialCombine the organic phases, dry (MgSO4)
  8. customevaporate the solvent in vacuo
  9. customrecrystallize (toluene)

Quellen und Nachweise

ORD-Eintrag
ord-73c1cb870d394d0a964bba97601fdf8f
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652370

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