HCID 178418361, compound → HCID 178507131, compound

HRID 2243323Notes

Reaction equation

HRID 2243323 reaction equation
[H][H].[F:3][C:4]([F:30])([F:29])[C:5]1[CH:28]=[CH:27][C:8]2[NH:9][C:10]([C:12]3[C:24]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[C:17](=[N:25]O)[C:16]=4[CH:15]=[CH:14][CH:13]=3)=[N:11][C:7]=2[CH:6]=1>C(O)C.O1CCCC1.[Ni]>[F:30][C:4]([F:3])([F:29])[C:5]1[CH:28]=[CH:27][C:8]2[NH:9][C:10]([C:12]3[C:24]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH:17]([NH2:25])[C:16]=4[CH:15]=[CH:14][CH:13]=3)=[N:11][C:7]=2[CH:6]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178526303HCID 178526303, compound

Product 1

HCID 178507131HCID 178507131, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The procedure used in Example 6 is followed. In a 528 ml autoclave, dissolve 2.2 g of 4-(5-trifluoromethyl-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 80 ml of ethanol and 80 ml of tetrahydrofuran, add a spatula of Raney activated nickel and then subject to an initial hydrogen pressure of 1 bar and heat the autoclave at 600 for 4 hours. After cooling, the volume of hydrogen absorbed is 412 ml. After filtration of the catalyst over Celite, concentrate under reduced pressure. In this way, we obtain 1.73 g of 4-(5-trifluoromethyl-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a grey foam with the following characteristics:

Workup

  1. additionadd a spatula of Raney
  2. temperatureheat the autoclave at 600 for 4 hours
  3. temperatureAfter cooling
  4. customthe volume of hydrogen absorbed
  5. filtrationAfter filtration of the catalyst over Celite
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-73f2773e8e434b07a45cc156528c2448
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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