Ammonia → 1-(4-Aminomethylphenyl)-3-(3-hydroxy-3-phenylpropyl)-4-(4-methoxyphenyl)azetidin-2-one

HRID 1007075Notes

Reaction equation

HRID 1007075 reaction equation
[OH:1][CH:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH:5]1[C:8](=[O:9])[N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH:6]1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.N.[H][H]>C(O)C.[Ni]>[NH2:15][CH2:14][C:13]1[CH:16]=[CH:17][C:10]([N:7]2[CH:6]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:5]([CH2:4][CH2:3][CH:2]([OH:1])[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:8]2=[O:9])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 226675944-[3-(3-Hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 159224861-(4-Aminomethylphenyl)-3-(3-hydroxy-3-phenylpropyl)-4-(4-methoxyphenyl)azetidin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

7 g of 4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]-benzonitrile are dissolved in 200 ml of ethanol and, after addition of 15 ml of concentrated ammonia, hydrogenated with 7 g of 50% aqueous Raney nickel under 50 bar of hydrogen. The crude product obtained after removal of the catalyst by filtration with suction and removal of the solvent in vacuo is purified on silica gel with dichloromethane/methanol/ammonia =200:10:1. The amine is obtained. MS (FAB, +LiCI): 423 (M+Li+) [C26H28N2O3 M=416].

Workup

  1. customThe crude product obtained
  2. customafter removal of the catalyst
  3. filtrationby filtration
  4. customwith suction and removal of the solvent in vacuo
  5. customis purified on silica gel with dichloromethane/methanol/ammonia =200:10:1

Sources & evidence

ORD record
ord-ea279d029f454a809ea1cda40cb18d85
Source dataset
uspto-grants-2004_09
Patent number
US06794359B2

Reaction notes

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