Phenethylamine → 2-(3-Oxo-1,2,3,4-tetrahydro-quinoxalin-2-yl)-N-phenethyl-acetamide

To the solution of (3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)-acetic acid (510 mg, 2.48 mmol) in THF (18 mL) was added triethylamine (0.38 ml, 2.74 mmol) and ethyl chloroformate (0.24 ml, 2.74 mmol). The mixture was stirred at rt for 1.5 hours and then phenethylamine (0.34 ml, 2.74 mmol) was added. The resulting mixture was again stirred at rt for 4.5 hours. The precipitate was filtered off and washed with small amount of THF a few times. The solvent was removed under the reduced pressure to give the title compound as a yellow solid: 1H NMR (DMSO-d6) δ=10.24 (bs, 1H), 8.03 (t, 1H, J=5.4 Hz), 7.30–7.15 (m, 5H), 6.75–6.70 (m, 3H), 6.61–6.56 (m, 1H), 5.79 (bs, 1H), 4.08–4.04 (m, 1H), 3.30–3.24 (m, 2H), 2.71 (t, 2H, J=7.8 Hz), 2.60 (dd, 1H, J=3.9, 15.3 Hz), 2.31 (dd, 1H, J=8.7, 15.3 Hz).

1. stirringThe resulting mixture was again stirred at rt for 4.5 hours
2. filtrationThe precipitate was filtered off
3. washwashed with small amount of THF a few times
4. customThe solvent was removed under the reduced pressure

ORD-Eintrag

ord-7044199215924cba96b3e1c29d5ddebe

Quelldatensatz

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07056937B2