Acetic Acid → 1-Benzyl-piperidin-4-yl 2-amino-4-bromo-benzoate

HRID 1291112Notes

Reaction equation

HRID 1291112 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([N+:24]([O-])=O)[CH:3]=1.C(O)(=O)C>C(O)C.[Fe]>[NH2:24][C:4]1[CH:3]=[C:2]([Br:1])[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

5

Reactant 2

HCID 176Acetic AcidHCID 189198501-Benzyl-piperidin-4-yl 4-bromo-2-nitro-benzoate

Product 1

HCID 189198111-Benzyl-piperidin-4-yl 2-amino-4-bromo-benzoateYield 106.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

0.42 g (0.001 mol) of 1-benzyl-piperidin-4-yl 4-bromo-2-nitro-benzoate was dissolved in 6 ml of ethanol and treated with 6 ml of glacial acetic acid and 0.225 g (0.004 mol) of iron powder. The mixture was boiled at reflux for 6 hrs. and concentrated and the residue was made basic with sat. sodium carbonate solution. The aqueous phase was extracted with ethyl acetate and the organic phase was washed with sat. sodium chloride solution and dried over sodium sulfate. After concentration the residue was chromatographed on silica gel with ethyl acetate/hexane (1:4). 0.415 g (100%) of 1-benzyl-piperidin-4-yl 2-amino-4-bromo-benzoate was obtained as white crystals.

Workup

  1. temperatureat reflux for 6 hrs
  2. concentrationand concentrated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe organic phase was washed with sat. sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationAfter concentration the residue
  7. customwas chromatographed on silica gel with ethyl acetate/hexane (1:4)

Sources & evidence

ORD record
ord-6d7d1391bb394d87b725e1453f07dfd4
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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