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

HRID 392828

Reaktionsgleichung

Reaktionsgleichung von HRID 392828
[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

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 65055N-BenzylphenethylamineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 8032171N-benzyl-N-(2-phenylethyl)acetamideAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7edcf815d4114aaa94c7bd9a5fb72a12
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803378B2

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