Dichloromethane → HCID 20316583, compound

HRID 2418997Notes

Reaction equation

HRID 2418997 reaction equation
[CH3:1][N:2]([CH3:25])[CH:3]([CH3:24])[CH2:4][C:5]([C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6](=[O:9])[CH2:7][CH3:8].C(Cl)Cl.B(Br)(Br)[Br:30].C(Cl)Cl>CO>[BrH:30].[CH3:25][N:2]([CH3:1])[CH:3]([CH3:24])[CH2:4][C:5]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6](=[O:9])[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 15709970HCID 15709970, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 20316583HCID 20316583, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 100 ml flask equipped for stirring, under a nitrogen atmosphere are placed 0.55g of 6-dimethylamino-4-(4-methoxyphenyl)-4-phenyl-heptane-3-one, 40 ml of methylene chloride and 12.1 ml of a solution of boron tribromide/methylene chloride (10% solution obtained commercially). The mixture was allowed to stir at room temperature overnight. Thereafter, 30 ml. of methanol was added with cooling. The residual oil, obtained upon removing the solvent at reduced pressure, was treated with 7 ml of water, whereupon the crude product crystallized. After filtration and washing with water, the solid was recrystallized from water to give 0.137 g of the above captioned product m.p. 246°-247.5° C. Concentration of the aqueous filtrate yielded a small second crop of 20 mg.

Workup

  1. customInto a 100 ml flask equipped
  2. customobtained commercially)
  3. stirringto stir at room temperature overnight
  4. temperaturewith cooling
  5. customThe residual oil, obtained
  6. customupon removing the solvent at reduced pressure
  7. additionwas treated with 7 ml of water, whereupon the crude product
  8. customcrystallized
  9. filtrationAfter filtration
  10. washwashing with water
  11. customthe solid was recrystallized from water
  12. customto give 0.137 g of the
  13. customConcentration of the aqueous filtrate yielded a small second crop of 20 mg

Sources & evidence

ORD record
ord-0876d7848ec0408bbd0d6c8412ad4e69
Source dataset
uspto-grants-1978_08
Patent number
US04104367

Reaction notes

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