Phenethylamine → HCID 10692987, compound

HRID 990706Notes

Reaction equation

HRID 990706 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3][CH:2]=1.[CH2:10]([O:17][C:18](=[O:30])[CH2:19][N:20]1[C:25]([CH3:26])=[C:24]([Cl:27])[N:23]=[C:22](Cl)[C:21]1=[O:29])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOC(C)=O>[CH2:10]([O:17][C:18](=[O:30])[CH2:19][N:20]1[C:25]([CH3:26])=[C:24]([Cl:27])[N:23]=[C:22]([NH:9][CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:21]1=[O:29])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate

Product 1

HCID 10692987HCID 10692987, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-Phenethylamine (0.38 ml, 3.0 mmol) was added to a stirred mixture of (3,5-dichloro-6-methyl-2-oxo-2H-pyrazin-1-yl)acetic acid benzyl ester (327 mg, 1.00 mmol) in EtOAc (2 ml) and the resulting mixture was heated to reflux under argon. After 2 h the reaction was cooled, diluted with EtOAc (the product is sparingly soluble), washed with 10% citric acid solution and brine, dried (Na2SO4) and evaporated in vacuo to give 1-3 as a crystalline solid. 1H NMR (CDCl3) δ2.21 (s, 3 H, CH3), 2.93 (t, J=7.1 Hz, 2 H, PhCH2), 3.67 (q, J=7.1 Hz, 2 H, CH2NH), 4.79 (s, 2 H, CH2), 5.21 (s, 2 H, CH2), 6.10 (br t, 1 H), 7.20-7.39 (m, 10 H, 2 Ph).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under argon
  3. temperatureAfter 2 h the reaction was cooled
  4. washwashed with 10% citric acid solution and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-82e9bd2b46244d7c91560834e2707bcc
Source dataset
uspto-grants-2002_10
Patent number
US06462050B1

Reaction notes

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