Methyl iodide → 3-[2-(N-isopropyl-N-methylamino)-propyl]-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

HRID 26430Notes

Reaction equation

HRID 26430 reaction equation
[CH:1]([NH:4][CH:5]([CH3:23])[CH2:6][C:7]1[C:8](=[O:22])[NH:9][CH2:10][CH2:11][CH2:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)([CH3:3])[CH3:2].CI.[C:26](=O)([O-])[O-].[K+].[K+]>C(O)C>[CH:1]([N:4]([CH:5]([CH3:23])[CH2:6][C:7]1[C:8](=[O:22])[NH:9][CH2:10][CH2:11][CH2:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH3:26])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20332938HCID 20332938, compound

Product 1

HCID 203329403-[2-(N-isopropyl-N-methylamino)-propyl]-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 8.23 g of 3-(2-isopropylaminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, 2.25 ml of methyl iodide, 3.59 g of potassium carbonate and 100 ml of absolute ethanol is refluxed for five hours and evaporated. The residue is suspended in 100 ml of water and the suspension extracted with diethyl ether. The extract is dried, evaporated and the residue crystallized from ethanol-water to yield the 3-[2-(N-isopropyl-N-methylamino)-propyl]-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone melting at 86°-88°.

Workup

  1. temperatureis refluxed for five hours
  2. customevaporated
  3. extractionthe suspension extracted with diethyl ether
  4. customThe extract is dried
  5. customevaporated
  6. customthe residue crystallized from ethanol-water

Sources & evidence

ORD record
ord-304a93c9702347f4af8e573ae0f35959
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Reaction notes

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