4-Nitrophenyl 1-oxo-1lambda~5~-pyridine-3-carboxylate → N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide

HRID 1981361Notes

Reaction equation

HRID 1981361 reaction equation
[N+:1]1([O-:19])[CH:6]=[CH:5][CH:4]=[C:3]([C:7](OC2C=CC([N+]([O-])=O)=CC=2)=[O:8])[CH:2]=1.[CH3:20][CH:21]1[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][C:28]2[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=2)[O:31][CH2:32][CH2:33][CH2:34][NH2:35])[CH2:22]1>CO>[CH3:20][CH:21]1[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][C:28]2[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=2)[O:31][CH2:32][CH2:33][CH2:34][NH:35][C:7]([C:3]2[CH:2]=[N+:1]([O-:19])[CH:6]=[CH:5][CH:4]=2)=[O:8])[CH2:22]1

Participants

4

Reactant 2

HCID 133646764-Nitrophenyl 1-oxo-1lambda~5~-pyridine-3-carboxylateHCID 140261883-{3-[(3-Methylpiperidin-1-yl)methyl]phenoxy}propan-1-amine

Product 1

HCID 6917813N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To the active ester thus obtained there is added a solution of 3.8 g of 3-[3-(3-methylpiperidinomethyl)phenoxy]propylamine in 70 ml of methanol and the mixture is stirred 3 hours at 50° C. The solvent is evaporated, the residue is taken up with 30 ml of N hydrochloric acid and the acid solution is washed 3 times with 20 ml of ethyl acetate. The pH is adjusted to 7.8, then the solution is salted out with sodium chloride and extracted 6 times with 30 ml of ethyl acetate. The organic extracts are collected and dried over anhydrous sodium sulfate and the solvent in evaporated to dryness. The product is purified by chromatography on silica as described in Example 7. Thus, the N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide is obtained, identical to the product of Example 8.

Workup

  1. customThe solvent is evaporated
  2. washthe acid solution is washed 3 times with 20 ml of ethyl acetate
  3. extractionextracted 6 times with 30 ml of ethyl acetate
  4. customThe organic extracts are collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent in evaporated to dryness
  7. customThe product is purified by chromatography on silica

Sources & evidence

ORD record
ord-29b42e2237774cae9ea78342356694ea
Source dataset
uspto-grants-1985_04
Patent number
US04514408

Reaction notes

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