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

HRID 392828

반응식

HRID 392828 반응식
[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

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 65055N-BenzylphenethylamineHCID 516892Sodium Bicarbonate

생성물 1

HCID 8032171N-benzyl-N-(2-phenylethyl)acetamide수율 102.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7edcf815d4114aaa94c7bd9a5fb72a12
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803378B2

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