Methyl iodide → N-(1-benzylpiperid-4-yl)-2-methoxy-4-amino-5-nitrobenzamide methyl iodide

HRID 1494535Notes

Reaction equation

HRID 1494535 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH2:25])=[CH:18][C:17]=2[O:26][CH3:27])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][I:30]>CC(C)=O.C(Cl)(Cl)Cl>[CH3:29][I:30].[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH2:25])=[CH:18][C:17]=2[O:26][CH3:27])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodide2×HCID 12821241N-(1-Benzylpiperid-4-yl)-2-methoxy-4-amino-5-nitrobenzamide

Product 1

HCID 19828533N-(1-benzylpiperid-4-yl)-2-methoxy-4-amino-5-nitrobenzamide methyl iodideYield 91.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

To a solution of N-(1-benzylpiperid-4-yl)-2-methoxy-4-amino-5-nitrobenzamide (3.8 g; 0.01 mole) [prepared as described in Example 1 or 4], in acetone (100 ml) and chloroform (100 ml), methyl iodide (1.25 ml; 0.02 moles) was added. After stirring at room temperature for 8 hours, an additional amount of methyl iodide (1.25 ml; 0.02 moles) was added and the mixture was left at room temperature for another 15 hours and then filtered. A solid was collected which was washed with diethyl ether to give 4.8 g of N-(1-benzylpiperid-4-yl)-2-methoxy-4-amino-5-nitrobenzamide methyl iodide. After recrystallization from a mixture of water-methanol, it melted at 232°-234° C. (dec).

Workup

  1. waitthe mixture was left at room temperature for another 15 hours
  2. filtrationfiltered
  3. customA solid was collected which
  4. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-cb57af0f8c1d460c8daed6c21aa5257a
Source dataset
uspto-grants-1991_06
Patent number
US05026858

Reaction notes

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