Water → HCID 20364450, compound

HRID 1678845Notes

Reaction equation

HRID 1678845 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:18][CH2:17][CH2:16][CH:15]=[C:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].S(O[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)(=O)(=O)C.O>CN(C)C=O>[CH3:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][N:12]2[C:11](=[O:20])[CH2:10][C:9]3([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)[C:14](=[CH:15][CH2:16][CH2:17][CH2:18]3)[C:13]2=[O:19])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12942077HCID 12942077, compoundHCID 132819714a-(m-Methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline

Product 1

HCID 20364450HCID 20364450, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4a-(m-Methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline (6 g) in 75 ml of anhydrous dimethylformamide was added to a 55% suspension of sodium hydride in mineral oil (1.2 g) in 50 ml of dimethylformamide at 70°. The reaction mixture was heated for one hour at 80° and then cooled to 25°. p-Methylphenethyl mesylate (7.0 g) was added and the reaction heated at 70° for 18 hours. It was poured into water and extracted with ether. The residue after evaporation of the ether was chromatographed on 800 g. of Florisil. This yielded 4.4 g, mp 134°-140°; recrystallized from ethanol, mp 149°-151°.

Workup

  1. temperatureThe reaction mixture was heated for one hour at 80°
  2. temperaturecooled to 25°
  3. temperaturethe reaction heated at 70° for 18 hours
  4. extractionextracted with ether
  5. customThe residue after evaporation of the ether
  6. customwas chromatographed on 800 g
  7. customrecrystallized from ethanol, mp 149°-151°

Sources & evidence

ORD record
ord-2dcaeb46f2c8445092c0000f26e8db7e
Source dataset
uspto-grants-1978_03
Patent number
US04077954

Reaction notes

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