1-Benzyl-piperidin-4-yl 4-iodo-2-nitrobenzoate → 1-Benzyi-piperidin-4-yl 4-iodo-2-amino-benzoate

HRID 1291118Notes

Reaction equation

HRID 1291118 reaction equation
[I: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)C.C(O)(=O)C.[Fe]>[I:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([O:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:13][CH2:14]2)=[O:7])=[C:4]([NH2:24])[CH:3]=1

Participants

5

Reactant 1

HCID 189197541-Benzyl-piperidin-4-yl 4-iodo-2-nitrobenzoate

Product 1

HCID 189197641-Benzyi-piperidin-4-yl 4-iodo-2-amino-benzoateYield 95%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

0.26 g (0.000588 mol) of 1-benzyl-piperidin-4-yl 4-iodo-2-nitro-benzoate was dissolved in 3.3 ml of ethanol, diluted with 3.3 ml of acetic acid and treated with 0.123 g (0.0022 mol) of iron powder. The mixture was boiled at reflux for 4 hrs., the solvent was distilled off, the residue was taken up in ethyl acetate, washed with saturated sodium carbonate solution and sodium chloride solution and the organic phase was dried over sodium sulfate. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:4) as the eluent. 0.232 g (95%) of 1-benzyi-piperidin-4-yl 4-iodo-2-amino-benzoate was obtained as a yellow oil. MS: me/e=437 (C19H22IN2O2 +).

Workup

  1. temperatureat reflux for 4 hrs
  2. distillation, the solvent was distilled off
  3. washwashed with saturated sodium carbonate solution and sodium chloride solution
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. customThe residue was chromatographed on silica gel with ethyl acetate/hexane (1:4) as the eluent

Sources & evidence

ORD record
ord-dcf673ddcf6b415f9c683b6886eb0eee
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

Loading…