Sodium borohydride → 2-(4-Diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanol

HRID 370660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 370660
[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[O:16])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:24]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=3)[OH:16])[CH2:12][CH2:13]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 103401292-(4-Diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanone

Produkt 1

HCID 30711602-(4-Diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanolAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In 50 ml of methanol was dissolved 3.0 g (7.8 mmol) of 2-(4-diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanone, to which 3.0 g (79 mmol) of sodium borohydride was added slowly under ice-cooled conditions. The reaction mixture was then stirred overnight at room temperature, and methanol was removed under reduced pressure. Thereafter, 100 ml of ether was added to the residue, and the solution was washed successively with water and saturated saline and dried over anhydrous sodium sulfate. The resultant ether solution was concentrated, and the residue was purified by silica gel column chromatography (silica gel 90 g; chloroform:methanol=100:1) to give 2.4 g of 2-(4-diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanol (yield: 79%) which, upon recrystallization from a mixed solvent of ethyl acetate and n-hexane, gave white crystals.

Aufarbeitung

  1. temperaturecooled conditions
  2. custommethanol was removed under reduced pressure
  3. additionThereafter, 100 ml of ether was added to the residue
  4. washthe solution was washed successively with water and saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe resultant ether solution was concentrated
  7. customthe residue was purified by silica gel column chromatography (silica gel 90 g; chloroform:methanol=100:1)

Quellen und Nachweise

ORD-Eintrag
ord-afb8743f98e245a082156e60b0db0e78
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04528194

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