Hydrochloric Acid → Hydroxyterfenadine

HRID 1018103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1018103
[O:1]=[C:2]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.[BH4-].[Na+].Cl>CO.O>[OH:1][CH:2]([C:26]1[CH:27]=[CH:28][C:29]([C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[CH:30][CH:31]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:25])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:7]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 118129062-(4-(1-Oxo-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-butyl)-phenyl)-2-methylpropanol

Produkt 1

HCID 9805485HydroxyterfenadineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Dissolve 2-(4-(1-oxo-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-butyl)-phenyl)-2-methylpropanol in methanol (450 mL) and stir for 15 minutes at room temperature. Add, by dropwise addition, a solution of sodium borohydride (2.25 g, 0.06 mol) in water (10 mL) over 15 minutes. Stir for another 30 minutes and cool in an ice-bath. Slowly add concentrated hydrochloric acid (4 mL) and water (8 mL) and stir for an additional 20 minutes. Evaporate the solvent in vacuo and partition the residue between methylene chloride (150 mL) and water (70 mL). Separate the organic phase and extract the aqueous phase with methylene chloride (25 mL). Wash the combined organic layers with water (2×50 mL), evaporate the solvent in vacuo and recrystallize (acetone) to give the title compound as white needles (9.53 g, 79%).

Aufarbeitung

  1. additionAdd, by dropwise addition
  2. stirringStir for another 30 minutes
  3. temperaturecool in an ice-bath
  4. stirringstir for an additional 20 minutes
  5. customEvaporate the solvent in vacuo
  6. custompartition the residue between methylene chloride (150 mL) and water (70 mL)
  7. customSeparate the organic phase
  8. extractionextract the aqueous phase with methylene chloride (25 mL)
  9. washWash the combined organic layers with water (2×50 mL)
  10. customevaporate the solvent in vacuo
  11. customrecrystallize (acetone)

Quellen und Nachweise

ORD-Eintrag
ord-989fcb9507484086a44455b32c10f532
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479663B2

Notizen zur Reaktion

Wird geladen…