HCID 18919843, compound → HCID 18919810, compound

HRID 1291070Notes

Reaction equation

HRID 1291070 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[C:7]([O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[O:8])([O-])=O>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[C:7]([O:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][CH2:15]1)=[O:8]

Participants

4

Reactant 1

HCID 18919843HCID 18919843, compound

Product 1

HCID 18919810HCID 18919810, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

0.5 g (0.00147 mol) of 1-benzyl-piperidin-4-yl 3-nitro-benzoate was dissolved in 20 ml of ethanol and treated with 0.3 g of Raney-nickel under argon. The mixture was hydrogenated at room temperature under normal pressure for 4 hrs. The catalyst was filtered off, the filtrate was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane 1:1 as the eluent. 0.372 g (82%) of 1-benzyl-piperidin-4-yl 3-amino-benzoate was obtained as white crystals; m.p. 70°-71°.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customthe residue was chromatographed over silica gel with ethyl acetate/hexane 1:1 as the eluent

Sources & evidence

ORD record
ord-93baf7dbd99140c682b9a9fc30a4526b
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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