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

HRID 342723ノート

反応式

HRID 342723 の反応式
[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]

参加物

5

反応物 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 1961175912-Methoxydodecanoyl chloride

生成物 1

HCID 979711912-Methoxy-N-(phenylmethyl)dodecanamide収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f3fdcc63ed540239232981c33639e1e
出典データセット
uspto-grants-1999_01
特許番号
US05859052

反応ノート

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