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

HRID 847591

Reaction equation

HRID 847591 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 22910035N-(1,5-Diphenylpent-3-yl)hydroxylamineYield 30.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 0.37 g (1.55 mmol) of 1,5-diphenyl-3-pentanone in 20 ml of 2-propanol was treated with 0.22g (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.

Workup

  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

Sources & evidence

ORD record
ord-44de30a433df468a9d7567e2a42897de
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Linked notes

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