Acetyl chloride → N-benzyl-N-(2-phenylethyl)acetamide

HRID 392828

反応式

HRID 392828 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[C:22](Cl)(=[O:24])[CH3:23]>C(Cl)Cl>[CH2:10]([N:9]([CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:22](=[O:24])[CH3:23])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 65055N-BenzylphenethylamineHCID 516892Sodium Bicarbonate

生成物 1

HCID 8032171N-benzyl-N-(2-phenylethyl)acetamide収率 102.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-benzyl-2-phenethylamine (2.2 g, 10 mmol) was dissolved in 7 mL of CH2Cl2. To this was added 7 mL of satd (aq.) NaHCO3 followed by acetyl chloride (0.88 g, 11 mmol) and the resulting mixture stirred for 40 min. The organic layer was separated, dried over Na2SO4 filtered and the solvent removed to yield 2.60 g (100%) oil. LC/MS (M+H) calcd for C17H20NO: 254.15; found: 254.07. 1H NMR and 13C NMR show a mixture of rotamers at room temperature. 1H NMR (500 MHz, CDCl3), δ: 2.04 (br s), 2.14 (br s), 2.81 (br m), 2.87 (br m), 3.44 (br m), 3.58 (br m), 4.36 (s), 4.62 (s), 7.11-7.36 (overlapping m, 10). 13C NMR (125 MHz, CDCl3) δ: 21.19, 21.80, 33.99, 34.87, 48.18, 48.28, 49.49, 52.75, 126.34, 126.81, 127.44, 127.65, 128.18, 128.52, 128.64, 128.73, 128.80, 128.85, 128.94, 136.74, 137.56, 138.17, 139.24, 170.81, 171.07.

後処理

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent removed

出典と根拠

ORDレコード
ord-7edcf815d4114aaa94c7bd9a5fb72a12
出典データセット
uspto-grants-2004_10
特許番号
US06803378B2

関連ノート

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