Water → (6-Bromo-quinoxalin-2-yl)-((R)-1-phenyl-ethyl)-amine

HRID 1020743Notes

Reaction equation

HRID 1020743 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[CH:6]=[N:5]2.[C:13]1([C@H:19]([NH2:21])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:21][C@@H:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:20])[CH:6]=[N:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 6431891-Phenethylamine, (+)-HCID 126864086-Bromo-2-chloroquinoxaline

Product 1

HCID 66797257(6-Bromo-quinoxalin-2-yl)-((R)-1-phenyl-ethyl)-amineYield 79.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-Bromo-2-chloro-quinoxaline (0.45 g, 1 eq, 1.85 mmol) in DMSO (6 mL), was added (R)-1-phenylethanamine (0.67 g, 3 eq, 5.55 mmol) at room temperature. The mixture was stirred overnight. After completion of the reaction (confirmed by TLC), cold water (40 mL) was added to the reaction mixture and this was stirred for 1 hour at room temperature. The precipitate was filtered off, washed with water (10 mL) and then dried under vacuum to afford the title compound (0.48 g, 79%).

Workup

  1. additionwas added to the reaction mixture
  2. stirringthis was stirred for 1 hour at room temperature
  3. filtrationThe precipitate was filtered off
  4. washwashed with water (10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0de0cbef06924422a5f8a88b2aea10df
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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