Benzylamine → 12-Methoxy-N-(phenylmethyl)dodecanamide

HRID 342723

반응식

HRID 342723 반응식
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32]>C(Cl)Cl>[CH3:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:32]

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 1961175912-Methoxydodecanoyl chloride

생성물 1

HCID 979711912-Methoxy-N-(phenylmethyl)dodecanamide수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of benzylamine (486mg, 4.5 mmol) in 20 mL of methylene chloride at 0° C. was added dropwise diisopropylethylamine (0.45 ml, 5 mmol) followed by the title product of example 11 (1.0 g, 4 mmol). After stirring at room temperature for 6 days, the reaction mixture was washed successively with 1N HCl, water, saturated NaHCO3, water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in anhydrous methanol and passed through a basic ion exchange resin and eluted with anhydrous methanol. Concentration afforded the title compound (895 mg) as a white solid, m.p. 77.7°-79.4° C. (DSC). The structure was supported by NMR, infrared spectroscopy, elemental analysis, and mass spectroscopy.

후처리

  1. washthe reaction mixture was washed successively with 1N HCl, water, saturated NaHCO3, water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in anhydrous methanol
  6. washeluted with anhydrous methanol
  7. concentrationConcentration

출처 및 근거

ORD 기록
ord-9f3fdcc63ed540239232981c33639e1e
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859052

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