Chloroacetic Acid → HCID 86592553, compound

HRID 1433046Notes

Reaction equation

HRID 1433046 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH2:8].Cl[CH2:10][C:11](O)=[O:12].C(=O)([O-])[O-].[K+].[K+]>O>[NH:1]1[C@@H:2]2[C@@H:3]([CH2:4][CH2:5][CH2:6][CH2:7]2)[NH:8][CH2:10][C:11]1=[O:12]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 11430Potassium CarbonateHCID 3429171,2-Diaminocyclohexane, cis-

Product 1

HCID 86592553HCID 86592553, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

cis-1,2-Diaminocyclohexane (4.1 g, 36 mmol) is dissolved in 150 ml of H2O. Chloroacetic acid (3.4 g, 36 mmol) in 50 ml of H2O is added dropwise at 10° C. in 5 minutes, then potassium carbonate (7.9 g, 57 mmol) in 30 ml of H2O is added dropwise at 10 C. The reaction mixture is allowed to warm slowly to room temperature and stirred 24 hours. The solution is heated at 90° C. for 2 hours, concentrated. The resulting solid is taken-up in boiling toluene (100 ml), filtered while hot, concentrated to give (+/−)-cis-decahydroquinoxalin-2-one (0.8 g, 14% yield) as a white solid. C8H14N2O, MS (M+H)+: 155

Workup

  1. temperatureThe solution is heated at 90° C. for 2 hours
  2. concentrationconcentrated
  3. filtrationfiltered while hot,
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-164cb69c90234ad6a61532031f404bfb
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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