Ammonia → 4-(4-Aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

HRID 132753Notes

Reaction equation

HRID 132753 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[CH:10]([CH2:13][CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[OH:16])[CH:9]2[C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[C:26]#N)=[CH:4][CH:3]=1.[H][H].[NH3:34]>C(O)C.[Ni]>[NH2:34][CH2:28][C:29]1[CH:30]=[CH:31][C:24]([CH:9]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:11](=[O:12])[CH:10]2[CH2:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[OH:16])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 22252073{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}-benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 222520324-(4-Aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

200 mg of {1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}-benzonitrile (16) were dissolved in 20 ml of ethanol and, with 0.5 ml of conc. ammonia, hydrogenated over Raney nickel at a hydrogen pressure of 75 bar and at 25° C. for 30 hours. The catalyst was filtered off with suction, the mixture was concentrated under reduced pressure and the residue was purified by column filtration (SiO2, CH2Cl2/methanol/conc. NH3=100:10:1). This gave the product of molecular weight 422.5 (C25H22F2N2O2); MS (DCI+): 423 (M+H+), 405 (M+H+-H2O).

Workup

  1. filtrationThe catalyst was filtered off with suction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. filtrationthe residue was purified by column filtration (SiO2, CH2Cl2/methanol/conc. NH3=100:10:1)
  4. customThis gave the product of molecular weight 422.5 (C25H22F2N2O2)

Sources & evidence

ORD record
ord-cc7848ad77f94df2a6a0b7767868c6ac
Source dataset
uspto-grants-2008_06
Patent number
US07388004B2

Reaction notes

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