HCID 18919779, compound → HCID 18919784, compound

HRID 1291160Notes

Reaction equation

HRID 1291160 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]=[CH:19][C:18]=2[N+:23]([O-])=O)[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[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 18919779HCID 18919779, compound

Product 1

HCID 18919784HCID 18919784, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

0.345 g (0.00101 mol) of 1-(2-nitro-benzyl)-piperidin-4-yl benzoate was dissolved in 15 ml of ethanol and treated with 0.2 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 (1:3) as the eluent. 0.197 g (61%) of 1-(2-amino-benzyl)-piperidin-4-yl benzoate was obtained as a colorless oil. MS: me/e=311 (C19H23N2 O2+).

Workup

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

Sources & evidence

ORD record
ord-9996ee1e2fe3427cb685f327936ef232
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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