HCID 18919872, compound → HCID 18919823, compound

HRID 1291072Notes

Reaction equation

HRID 1291072 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[C:6]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:7])([O-])=O>C(O)C.[Ni]>[NH2:1][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[C:6]([O:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:13][CH2:14]1)=[O:7]

Participants

4

Reactant 1

HCID 18919872HCID 18919872, compound

Product 1

HCID 18919823HCID 18919823, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

0.5 g (0.00147 mol) of 1-benzyl-piperidin-4-yl 2-nitro-benzoate was dissolved in 20 ml of ethanol and treated with 0.05 g of Raney-nickel. The mixture was hydrogenated at room temperature under normal pressure for 24 hrs. The catalyst was filtered off and the solvent was removed completely. The residue was chromatographed over silica gel with ethyl acetate/hexane (1:1) as the eluent. 0.322 g (71%) of 1-benzyl-piperidin-4-yl 2-amino-benzoate was obtained as yellow crystals; m.p. 87°-88°.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed completely
  3. customThe residue was chromatographed over silica gel with ethyl acetate/hexane (1:1) as the eluent

Sources & evidence

ORD record
ord-3fe9e4616bdd4336bc41a614e683e724
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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