1,5-Diphenylpentan-3-one → N-(1,5-Diphenylpent-3-yl)hydroxylamine

HRID 1379345

Reaktionsgleichung

Reaktionsgleichung von HRID 1379345
[C:1]1([CH2:7][CH2:8][C:9](=O)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:20][OH:21].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CC(O)C>[C:1]1([CH2:7][CH2:8][CH:9]([NH:20][OH:21])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 214961,5-Diphenylpentan-3-oneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 22910035N-(1,5-Diphenylpent-3-yl)hydroxylamineAusbeute 30,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 0.37 g (1.55 mmol) of 1,5-diphenyl-3-pentanone in 20 ml of 2-propanol was treated with 0.22 g (3.1 mmol) of hydroxylamine hydrochloride and 0.31 g (4.7 mmol) of anhydrous sodium acetate. After being stirred for 10 min, the mixture was treated with 0.20 g (3.2 mmol) of sodium cyanoborohydride and stirred at ambient temperature for 16 h. After concentration in vacuo, the residue was taken up in ethyl acetate, washed sequentially with aqueous NaHCO3 and saturated brine, dried over MgSO4, and concentrated. Flash chromatography using 40% ethyl acetate in chloroform gave 121 mg (31%) of the desired compound (Rf 0.16, 30% ethyl acetate in chloroform) as a white solid, m.p. 54°-55° C. 1H NMR (CDCl3) δ 1.7-1.85 (m, 2H), 1.85-2.0 (m, 2H), 2.6-2.75 (m, 4H), 2.90 (pentet, J=6 Hz, 1H), 5.22 (br, 2H), 7.1-7.35 (m, 10H). Mass spectrum (M+H)+ =256.

Aufarbeitung

  1. stirringstirred at ambient temperature for 16 h
  2. concentrationAfter concentration in vacuo
  3. washwashed sequentially with aqueous NaHCO3 and saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f673414ec35f489f9b70cc58d6336ffc
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05670675

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