Sodium Iodide → Diethyl 2-amino-6-[(2-oxo-2-piperidin-1-yl-ethoxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate

HRID 1954339Notes

Reaction equation

HRID 1954339 reaction equation
[Na].[NH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:18][C:19](=[O:22])[NH:20][OH:21])[CH:9]=[CH:10]2)[C:4]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl[CH2:29][C:30]([N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31].[I-].[Na+]>CO>[NH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:18][C:19](=[O:22])[NH:20][O:21][CH2:29][C:30](=[O:31])[N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[CH:9]=[CH:10]2)[C:4]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 2223122-Chloro-1-piperidine-1-yl-ethanoneHCID 86755843Diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate sodium

Product 1

HCID 15411819Diethyl 2-amino-6-[(2-oxo-2-piperidin-1-yl-ethoxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.96 g (2.5 mmol) of diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate sodium, 50 ml of methanol, 0.4 g (2.5 mmol) of N-chloroacetyl-piperidine and 20 mg of sodium iodide is heated at reflux for 20 hours. Thereafter, the mixture is concentrated and the residue is chromatographed on silica gel. Elution with isohexane: ethyl acetate 1:1 gives 0.42 g (35% of theory) of the title compound of m.p. 153-155° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 20 hours
  3. concentrationThereafter, the mixture is concentrated
  4. customthe residue is chromatographed on silica gel
  5. washElution with isohexane: ethyl acetate 1:1

Sources & evidence

ORD record
ord-d122489b98a24072a81d759f71729e94
Source dataset
uspto-grants-2000_09
Patent number
US06121322

Reaction notes

Loading…