Triethylamine → 1-Benzyl-piperidin-4-yl 4-iodo-2-nitrobenzoate

HRID 1291117Notes

Reaction equation

HRID 1291117 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH2:27]([N:34]1[CH2:39][CH2:38][CH:37](O)[CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH:37]2[CH2:36][CH2:35][N:34]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:39][CH2:38]2)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 784611-Benzylpiperidin-4-olHCID 189198834-Iodo-2-nitrobenzoic acid

Product 1

HCID 189197541-Benzyl-piperidin-4-yl 4-iodo-2-nitrobenzoateYield 13%

Procedure

2.33 g (0.00795 mol) of 4-iodo-2-nitrobenzoic acid were boiled und reflux in 13.8 ml (0.16 mol) of oxalyl chloride for 3 hrs. After removal of the excess oxalyl chloride the mixture was concentrated twice with 30 ml of toluene each time. The residue was dissolved in 80 ml of toluene, treated with 1.94 ml (0.0139 mol) of triethylamine and 1.52 g (0.00795 mol) of 1-benzyl-4-hydroxypiperidine and boiled at reflux for 18 hrs. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane (1:3). 0.465 g (13%) of 1-benzyl-piperidin-4-yl 4-iodo-2-nitrobenzoate was obtained as a yellow oil. MS: me/e=467 (C19H20IN2O4 +).

Workup

  1. customAfter removal of the excess oxalyl chloride the mixture
  2. concentrationwas concentrated twice with 30 ml of toluene each time
  3. dissolutionThe residue was dissolved in 80 ml of toluene
  4. temperatureat reflux for 18 hrs
  5. customAfter removal of the solvent the residue
  6. customwas chromatographed on silica gel with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-805d4621af5a4fdeb907d30afc524839
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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