HCID 18919836, compound → HCID 18919818, compound

HRID 1291171Notes

Reaction equation

HRID 1291171 reaction equation
[CH3:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1>C(O)C.[Ni]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=3)[CH2:13][CH2:14]2)=[O:7])=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 18919836HCID 18919836, compound

Product 1

HCID 18919818HCID 18919818, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

0.48 g (0.00135 mol) of 1-(4-nitro-benzyl)-piperidin-4-yl 4-methyl-benzoate was dissolved in 27 ml of ethanol and treated with 0.48 g of Raney-nickel. The mixture was hydrogenated at room temperature and under normal pressure for 3 hrs. The catalyst was filtered off and, after concentration, the residue was chromatographed on silica gel with ethyl acetate/hexane (1:1→5:2) as the eluent. 0.405 g (92.5%) of 1-(4-amino-benzyl)-piperidin-4-yl 4-methyl-benzoate was obtained as a yellowish oil. MS: me/e=325 (C20H25N2O2+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationafter concentration
  3. customthe residue was chromatographed on silica gel with ethyl acetate/hexane (1:1→5:2) as the eluent

Sources & evidence

ORD record
ord-f6d7f92dcc2b4359ae2735facbc79540
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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