HCID 18919855, compound → HCID 18919852, compound

HRID 1291165Notes

Reaction equation

HRID 1291165 reaction equation
[C:1]([O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=2)[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Ni]>[C:1]([O:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=2)[CH2:14][CH2:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18919855HCID 18919855, compound

Product 1

HCID 18919852HCID 18919852, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

0.207 g (0.0006 mol) of 1-(3-nitro-benzyl)-piperidin-4-yl benzoate was dissolved in 12 ml of ethanol and treated with 0.12 g of Raney-nickel. The mixture was hydrogenated at room temperature and under normal pressure for 8 hrs. The catalyst was filtered off and, after concentration, the residue was chromatographed on silica gel with ethyl acetate/hexane (1:1) as the eluent. 0.097 g (52%) of 1-(3-amino-benzyl)-piperidin-4-yl benzoate was obtained as yellowish crystals; m.p. 95°-97°.

Workup

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

Sources & evidence

ORD record
ord-53f5df3fbe4945d28451aa189d0d9ef1
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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