1,1'-Carbonyldiimidazole → N-methoxy-N-methyl-1-(4-nitrophenyl)piperidine-4-carboxamide

HRID 2236830Notes

Reaction equation

HRID 2236830 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:32][NH:33][O:34][CH3:35]>ClCCl>[CH3:35][O:34][N:33]([CH3:32])[C:16]([CH:13]1[CH2:12][CH2:11][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:15][CH2:14]1)=[O:18]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27672651-(4-Nitrophenyl)piperidine-4-carboxylic acid

Product 1

HCID 86098660N-methoxy-N-methyl-1-(4-nitrophenyl)piperidine-4-carboxamideYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 1-(4-nitrophenyl)piperidine-4-carboxylic acid (0.76 g, 3.0 mmol) in dichloromethane (15 mL) is cooled to 0° C. in an ice-water bath. Carbonyldiimidazole (0.59 g, 3.6 mmol) is added and the mixture is allowed to warm to room temperature. An additional volume of dichloromethane (10 mL) is added and the mixture continued to stir for 30 minutes before the addition of N,O-dimethylhydroxylamine hydrochloride (0.73 g, 7.5 mmol). After stirring overnight, the reaction mixture is filtered. The insoluble material is washed with diethyl ether, and the combined filtrate is washed with 5% aqueous potassium hydrogen carbonate solution, water, and saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 1-(4-nitro-phenyl)-piperidine-4-carboxylic acid methoxy-methyl-amide as a bright yellow powder (0.84 g, 95%).

Workup

  1. temperatureto warm to room temperature
  2. filtrationthe reaction mixture is filtered
  3. washThe insoluble material is washed with diethyl ether
  4. washthe combined filtrate is washed with 5% aqueous potassium hydrogen carbonate solution, water, and saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91344abd1e634a95a8a50ccb2811e1db
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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