Phenethyl bromide → N-Phenethyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

HRID 26479

Reaction equation

HRID 26479 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].CCCCC.[CH2:28](Br)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O>[CH2:28]([N:12]1[C:11](=[O:20])[CH2:10][C@@:9]2([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C@H:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[C:13]1=[O:19])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 8003PentaneHCID 24758Sodium hydrideHCID 867364784a-(m-Methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

Product 1

HCID 13282015N-Phenethyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 10.0 g (37 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline in 250 ml of anhydrous dimethylformamide was added with stirring to a suspension of 2.8 g (55.5 mmoles) of 50% sodium hydride in mineral oil (washed with pentane) in 125 ml of anhydrous dimethylformamide heated at 50° under nitrogen. The mixture was heated at 90° for 2 hours, then cooled to 40°, at which time a solution of 14.0 g (74 mmoles) of phenethyl bromide in 20 ml of anhydrous dimethylformamide was added and the reaction mixture heated at 90° overnight. The cooled solution was poured into ice-water and extracted with ether. Evaporation of the ether gave an oil which was purified by column chromatography (Silicar CC-7, eluting with acetone-benzene). The major fraction was identified as N-phenethyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline.

Workup

  1. temperatureheated at 50° under nitrogen
  2. temperatureThe mixture was heated at 90° for 2 hours
  3. additionwas added
  4. temperaturethe reaction mixture heated at 90° overnight
  5. extractionextracted with ether
  6. customEvaporation of the ether
  7. customgave an oil which
  8. customwas purified by column chromatography (Silicar CC-7, eluting with acetone-benzene)

Sources & evidence

ORD record
ord-39d377ee3df3459fbf811c3daf211de4
Source dataset
uspto-grants-1979_04
Patent number
US04150135

Linked notes

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