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, SH), 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-a789455f285645faba14f4b436a77c59

Quelldatensatz

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07635775B2