Methyl iodide → N-(1-Cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide methyl iodide

HRID 261056Notes

Reaction equation

HRID 261056 reaction equation
[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:29])[C:16]3[CH:21]=[C:20]([Cl:22])[C:19]([NH:23][C:24](=[O:26])[CH3:25])=[CH:18][C:17]=3[O:27][CH3:28])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:30][I:31]>C(OCC)C>[CH3:30][I:31].[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:29])[C:16]3[CH:21]=[C:20]([Cl:22])[C:19]([NH:23][C:24](=[O:26])[CH3:25])=[CH:18][C:17]=3[O:27][CH3:28])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 20395820N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide

Product 1

HCID 20395854N-(1-Cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide methyl iodideYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a warm solution of N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide (10 g; 0.023 moles) in diethyl ether (300 ml) a solution of methyl iodide (1.8 ml; 0.033 moles) in diethyl ether (25 ml) was added. The mixture was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. An additional amount of methyl iodide (1 g; 0.0023 moles) was added and the reflux of the mixture was kept up for 3 more hours. The mixture was then evaporated in vacuo and the residue recrystallized from a mixture of diethyl ether-ethanol. N-(1-Cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide methyl iodide (10.5 g), m.p. 209°-211° C., was thus obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe reflux of the mixture
  4. customThe mixture was then evaporated in vacuo
  5. customthe residue recrystallized from a mixture of diethyl ether-ethanol

Sources & evidence

ORD record
ord-245edea56c724f049ffaff5fe769e982
Source dataset
uspto-grants-1979_08
Patent number
US04163789

Reaction notes

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