O-Methyltyramine → N-(2-(4-Methoxyphenyl)ethyl)acetamide

HRID 551598

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]=1

Participants

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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947761B2

Linked notes

Loading…