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

HRID 350677Notes

Reaction equation

HRID 350677 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]1[CH2:12][C:13]([OH:15])=O.C(N(CC)CC)C.ClC(OCC)=O.[CH2:29]([NH2:37])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]1[CH2:12][C:13]([NH:37][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:15]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 2783994(3-Oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)acetic acid

Product 1

HCID 31559142-(3-Oxo-1,2,3,4-tetrahydro-quinoxalin-2-yl)-N-phenethyl-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-edf2c90c829149d1bc3368b071117e9f
Source dataset
uspto-grants-2007_02
Patent number
US07183281B2

Reaction notes

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