1,5-Diphenylpentan-3-one → 1,5-Diphenylpentan-3-amine

HRID 565420

반응식

HRID 565420 반응식
[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.C([O-])(=O)C.[NH4+].C([O-])(=O)C.[Na+].C([BH3-])#[N:30].[Na+]>CO>[CH2:8]([CH:9]([NH2:30])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 214961,5-Diphenylpentan-3-oneHCID 517045Sodium AcetateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 153888741,5-Diphenylpentan-3-amine

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a solution of 1,5-Diphenylpentan-3-one (5.26 g, 22.1 mmol), ammonium acetate (8.52 g, 110.5 mmol) and sodium acetate (9.06 g, 110.5 mmol) in methanol (80 mL) was added a solution of sodium cyanoborohydride (1.67 g, 26.52 mmol) in methanol (20 mL) and the reaction heated to reflux. After stirring at reflux for 30 min, the reaction was cooled and concentrated to dryness. The residue was partioned between methylene chloride and 2N sodium hydroxide. The organic phase was separated, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Chromatography of the residue on silica gel (elution with 2-5% methanol/methylene chloride) provided N-(1-phenethyl-3-phenyl-propyl)amine. To a solution of the above amine (2.1 g, 8.82 mmol) in ethanol (50 mL), was added 2-imidazole-carboxaldehyde (813 mg, 8.47 mmol) and the reaction heated to 50° C. After stirring for 2 hr, the resulting homogeneous solution was treated with sodium borohydride (400 mg, 10.58 mmol) and allowed to stir overnight. The reaction was concentrated to dryness and the residue was partioned between methylene chloride and 2N sodium hydroxide. The organic phase was separated, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Chromatography of the residue on silica gel (elution with 5% methanol/methylene chloride) provided compound 22.

후처리

  1. temperaturethe reaction heated to reflux
  2. temperatureat reflux for 30 min
  3. temperaturethe reaction was cooled
  4. concentrationconcentrated to dryness
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-69139821fb454271945d8180eabb619d
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172086B2

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