HCID 137252519, compound → HCID 44184979, compound

HRID 1695560Notes

Reaction equation

HRID 1695560 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[N:19]O)[C:10]=2[CH:9]=[CH:8][CH:7]=1>C(O)C.O1CCCC1.[Ni]>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]([NH2:19])[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 137252519HCID 137252519, compound

Product 1

HCID 44184979HCID 44184979, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Work in an autoclave as in Stage 3 in Example 5, starting from 449 mg of equimolecular mixture of the Z and E isomers of 4-(1H-imidazol-2-yl)-fluoren-9-one oxime, obtained in the preceding stage, in a mixture of 25 mL of ethanol and 25 mL of tetrahydrofuran, in the presence of Raney nickel, under an initial hydrogen pressure of 1 bar, at 60° C. for 3 hours. After filtration of the catalyst on Celite, concentration of the filtrate at reduced pressure and purification by making into a paste with diisopropyl oxide, we obtain 367 mg of 4-(1H-imidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a white powder, with the following characteristics:

Workup

  1. filtrationAfter filtration of the catalyst on Celite, concentration of the filtrate
  2. customat reduced pressure and purification

Sources & evidence

ORD record
ord-bd0978d050904e37816113e05fdc80c4
Source dataset
uspto-grants-2012_04
Patent number
US08163750B2

Reaction notes

Loading…