Dimethyl Sulfate → hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

HRID 2049321Notes

Reaction equation

HRID 2049321 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]2=[O:16])[CH:5]=[CH:6][CH:7]=1.S(OC)(O[CH3:21])(=O)=O>[OH-].[Na+]>[CH3:21][O:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]2=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 11746121hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

Product 1

HCID 2727906hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-oneYield 72.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one (21.9 g) was dissolved in 2 M sodium hydroxide solution (100 ml) and dimethyl sulphate (18.3 g, 14.5 ml) added. The reaction mixture was stirred at room temperature for 10 minutes then seeded. The product crystallised after leaving at 0° C. for 3 hours. The product was filtered, washed with water and dried affording 16.99 g of title compound as off-white powder m.p. 73°-74° C., identical to that obtained in Example 2.

Workup

  1. customThe product crystallised
  2. customafter leaving at 0° C. for 3 hours
  3. filtrationThe product was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-da49fcdf1a564c1a8f5086a8ec89f05b
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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