Water → HCID 20313224, compound

HRID 2420169Notes

Reaction equation

HRID 2420169 reaction equation
[CH:1]([NH:4][CH2:5][CH:6]([OH:20])[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=O)[CH2:13][CH:12]2[CH3:19])([CH3:3])[CH3:2].C(Cl)Cl.C(N(CC)CC)C.Br[CH2:32][C:33](Br)=[O:34].[OH2:36]>C1C=CC=CC=1>[CH:1]([N:4]1[C:33](=[O:34])[CH2:32][O:20][CH:6]([C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][CH2:13][CH:12]3[CH3:19])=[O:36])[CH2:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 12800271HCID 12800271, compound

Product 1

HCID 20313224HCID 20313224, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture of 2.77 g. of 3-isopropylamino-1-(3-methyl-1-oxo-5-indanyloxy)-2-propanol, 50 ml. of methylene chloride, and 1.2 g. of triethylamine was added dropwise 2.1 g. of bromoacetyl bromide with stirring under ice-cooling and the mixture was stirred for 18 hours at room temperature. Thereafter, methylene chloride was distilled off and after adding to the residue formed 50 ml. of benzene and 50 ml. of water to form a solution, the benzene layer formed was recovered, washed with 20 ml. of aqueous 5% hydrochloric acid solution and then twice each with 30 ml. of water, dried over anhydrous magnesium sulfate. Then, benzene was distilled off from the reaction mixture and after adding to the residue a solution of 0.3 g. of metallic sodium in 50 ml. of methanol, the mixture was refluxed for 3 hours. Methanol was distilled off and then to the residue were added 50 ml. of benzene and 30 ml. of water. The benzene layer formed was recovered from the mixture, washed twice with 20 ml. of aqueous 5% hydrochloric acid solution and then 20 ml. of water, and dried over anhydrous magnesium sulfate. Then, benzene was distilled off and 2 ml. of acetone was added to the residue to form precipitates, which were recovered by filtration. Thus, 2.3 g. (yield 73.6%) of 4-isopropyl-2-(3-methyl-1-oxo-5-indanyloxymethyl)-5-oxomorpholine was obtained. By recrystallizing the product from acetone, the faint yellow crystals of the product melting 150°-152° C. were obtained.

Workup

  1. additionTo a mixture of 2.77 g
  2. temperaturecooling
  3. distillationThereafter, methylene chloride was distilled off
  4. additionafter adding to the residue
  5. customformed 50 ml
  6. customwas recovered
  7. washwashed with 20 ml
  8. dry with materialof water, dried over anhydrous magnesium sulfate
  9. distillationThen, benzene was distilled off from the reaction mixture
  10. additionafter adding to the residue a solution of 0.3 g
  11. temperatureof methanol, the mixture was refluxed for 3 hours
  12. distillationMethanol was distilled off
  13. additionto the residue were added 50 ml
  14. customThe benzene layer formed
  15. customwas recovered from the mixture
  16. washwashed twice with 20 ml
  17. dry with materialof water, and dried over anhydrous magnesium sulfate
  18. distillationThen, benzene was distilled off
  19. additionof acetone was added to the residue
  20. customto form
  21. customprecipitates
  22. filtrationwhich were recovered by filtration

Sources & evidence

ORD record
ord-6690286808c2443798365c370b54f6ae
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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