Water → 3-[3-(Benzyloxy)phenyl]-2-azepanone

HRID 2049331Notes

Reaction equation

HRID 2049331 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 126655233-(3-hydroxyphenyl)hexahydro-2H-azepin-2-one

Product 1

HCID 129266083-[3-(Benzyloxy)phenyl]-2-azepanoneYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-hydroxyphenyl)hexahydro-2H-azepin-2-one (2.05 g) in dry DMF was added dropwise to a suspension of sodium hydride (0.3 g). After 30 minutes at ambient temperature, benzyl chloride (1.3 g) was added. The mixture was stirred for a further 2 hours and then cooled, and treated with water. The resulting solution was extracted several times with toluene, and the combined toluene layers washed thoroughly with water. The solvent was evaporated to give an oil that crystallised from ethyl acetate to give the title compound as a white solid (1.4 g) m.p. 119°-122° C.

Workup

  1. temperaturecooled
  2. extractionThe resulting solution was extracted several times with toluene
  3. washthe combined toluene layers washed thoroughly with water
  4. customThe solvent was evaporated
  5. customto give an oil that
  6. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-96d55f6e1fc0424bb7ba325fe121d9f2
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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