Ethanol → 1,3-Dimethyl-4-p-methoxyphenoxy-hexahydroazepine

HRID 28123Notes

Reaction equation

HRID 28123 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:4]([CH3:17])[CH2:3]1.[OH-].[K+].[CH2:20](O)C>>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH:5]([O:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:20])=[CH:14][CH:15]=2)[CH:4]([CH3:17])[CH2:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 23339238HCID 23339238, compound

Product 1

HCID 233392741,3-Dimethyl-4-p-methoxyphenoxy-hexahydroazepine

Procedure

23.5 g of 1,3-dimethyl-4-p-hydroxyphenoxy-hexahydroazepine are dissolved in 100 ml of absolute ethanol, 200 ml of 0.5 N ethanolic KOH are added, the reaction mixture is stirred for one hour at 20° and evaporated and the residue is taken up in 250 ml of absolute DMF. 12.6 g of dimethyl sulfate are added in portions, while stirring. The mixture is boiled for 2 hours and evaporated and the residue is worked up in the customary manner, giving 1,3-dimethyl-4-p-methoxyphenoxy-hexahydroazepine, 2 oily isomers, Rf 0.36 and 0.55.

Workup

  1. customevaporated
  2. addition12.6 g of dimethyl sulfate are added in portions
  3. stirringwhile stirring
  4. waitThe mixture is boiled for 2 hours
  5. customevaporated

Sources & evidence

ORD record
ord-6a1bba5d27e84609bc163f19a2093dbc
Source dataset
uspto-grants-1980_09
Patent number
US04225608

Reaction notes

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