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

HRID 392828

Reaction equation

HRID 392828 reaction equation
[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

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 65055N-BenzylphenethylamineHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-7edcf815d4114aaa94c7bd9a5fb72a12
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Linked notes

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