HCID 18919914, compound → HCID 18919885, compound

HRID 1291121Notes

Reaction equation

HRID 1291121 reaction equation
[NH2:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[C:4]([O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:5]>C(O)C.[Ni]>[NH2:1][C:2]1[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:3]=1[C:4]([O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:5]

Participants

4

Reactant 1

HCID 18919914HCID 18919914, compound

Product 1

HCID 18919885HCID 18919885, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

0.19 g (0.000537 mol) of 1-benzyl-piperidin-4-yl 2-amino-4-nitro-benzoate was dissolved in 16 ml of ethanol, treated with 0.115 g of Raney-Nickel and hydrogenated under normal pressure. The catalyst was filtered off, the solvent was removed on a rotary evaporator and the residue was chromatoraphed on silica gel with ethyl acetate/hexane (1:1→1:1) as the eluent. 0.155 g (89%) of 1-benzyl-piperidin-4-yl 2,4-diamino-benzoate was obtained as white crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-f6a888da6cc14100b7c2577ca9a7ad98
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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