HCID 18919793, compound → HCID 18919759, compound

HRID 1291110Notes

Reaction equation

HRID 1291110 reaction equation
[N+:1]([C:4]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[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]=[C:24]([C:26]([F:29])([F:27])[F:28])[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]

Participants

4

Reactant 1

HCID 18919793HCID 18919793, compound

Product 1

HCID 18919759HCID 18919759, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

0.25 g (0.000612 mol) of 1-benzyl-piperidin-4-yl 2-nitro-4-trifluoromethyl-benzoate was dissolved in 10 ml of ethanol and treated with 0.15 g of Raney-nickel. The mixture was hydrogenated at room temperature under normal pressure for 2 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. 0.11 g (48%) of 1-benzyl-piperidin-4-yl 2-amino-4-trifluoromethyl-benzoate was obtained as a yellow oil. MS: me/e=379 (C20H22F3N2 O2 +).

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-9f0de566935c464695a3f1965bfc71a3
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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