1,2-Diaminocyclohexane, trans- → HCID 57567898, compound

HRID 556218Notes

Reaction equation

HRID 556218 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=O)=O)=[CH:4][CH:3]=1.[C@@H:19]1([NH2:26])[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]1[NH2:25]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:26][CH:19]3[CH:20]([CH2:21][CH2:22][CH2:23][CH2:24]3)[N:25]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 438061,2-Diaminocyclohexane, trans-HCID 1230724,4'-Difluorobenzil

Product 1

HCID 57567898HCID 57567898, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 12.07 g of 4,4′-difluorobenzil (manufactured by Tokyo Kasei Kogyo Co., Ltd) was mixed with 5.60 g of trans-1,2-cyclohexanediamine (manufactured by Kanto Kasei Co., Ltd) by using 300 mL of ethanol as a solvent, and then the mixed solution was refluxed under a nitrogen atmosphere for 3 hours. By leaving a the refluxed solution to be cooled to a room temperature and taking out a deposited crystal by filtration, 2,3-bis(4-fluorophenyl)-4a,5,6,7,8,8a-hexahydroquinoxaline was obtained (light yellow plate-like crystal, yield: 94%). Subsequently, 6.90 g of 2,3-bis(4-fluorophenyl)-4a,5,6,7,8,8a-hexahydroquinoxaline which was obtained in the above step was mixed with 6.90 g of iron chloride (III) using 150 mL of ethanol as a solvent to gently stir with heat for 3 hours at 50° C. After the stirring, a deposition was caused by adding water to the stirred solution. A deposit was taken out by filtering and was washed with ethanol. Then, by recrystallizing the deposit with ethanol, a ligand 2,3-bis(4-fluorophenyl)-5,6,7,8-tetrahydroquinoxaline (abbreviation: HfdpqtH) was obtained (milky white powder, yield: 68%). Synthesis scheme of Step 1 (e-1) is shown next.

Workup

  1. temperaturethe mixed solution was refluxed under a nitrogen atmosphere for 3 hours
  2. customBy leaving a the refluxed solution
  3. filtrationby filtration

Sources & evidence

ORD record
ord-c3fafa3eddf6402db04df763bd1f43d6
Source dataset
uspto-grants-2011_11
Patent number
US08053974B2

Reaction notes

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