O-Methyltyramine → N-(2-(4-Methoxyphenyl)ethyl)acetamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][CH:4]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To 100 g of 2-(4-methoxyphenyl)ethylamine in 500 mL of chloroform was slowly added 100 mL of triethylamine acetic anhydride (72 g), and this was stirred at 20° C. for 40 minutes. The mixture was then extracted twice with a dilute aqueous solution of HCl (0.4 N, 400 mL) followed by a saturated aqueous solution of NaHCO3 (2×400 mL). The solvent was removed by rotary evaporation, and the residue was dried in a vacuum oven (45° C.), resulting in an off-white powder, N-[2-(4-methoxyphenyl)ethyl]acetamide (120 g, 93.9% yield). 1HNMR (DMSO-d6) spectrum was consistent with the desired product.
Workup
- extractionThe mixture was then extracted twice with a dilute aqueous solution of HCl (0.4 N, 400 mL)
- customThe solvent was removed by rotary evaporation
- customthe residue was dried in a vacuum oven (45° C.)
Sources & evidence
- ORD record
- ord-7f18dbd5d4574d86b7596e5827db9451
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947761B2
Reaction notes
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