HCID 136385276, compound → HCID 67360096, compound

HRID 2243368Notes

Reaction equation

HRID 2243368 reaction equation
[H][H].[CH3:3][C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[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)[NH:9][C:8]=2[CH:27]=1>C(O)C.O1CCCC1.[Ni]>[CH3:3][C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[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)[NH:9][C:8]=2[CH:27]=1

Participants

6

Reactant 2

HCID 136385276HCID 136385276, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67360096HCID 67360096, compoundYield 75.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The procedure used in Example 6 is followed. In a 100 ml autoclave, dissolve 1 g of 4-(6-methyl-1H-benzimidazol-2-yl)-9H-fluoren -9-one oxime (Z,E), obtained in the previous stage, in a mixture of 40 ml of ethanol and 40 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 60° C. for 3 hours. After cooling, the volume of hydrogen absorbed is 142 ml. After filtration of the catalyst over Celite, the filtrate is concentrated under reduced pressure and then taken up in petroleum ether and filtered. In this way, we obtain 720 mg of 4-(6-methyl-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a beige solid, which is used as it is in the following stage, with the following characteristic:

Workup

  1. additionadd a spatula of Raney
  2. temperatureAfter cooling
  3. customthe volume of hydrogen absorbed
  4. filtrationAfter filtration of the catalyst over Celite
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b19e22c0770e47dfb8a285e8e11616b3
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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