Water → HCID 70624490, compound

HRID 2420175Notes

Reaction equation

HRID 2420175 reaction equation
Br[CH2:2][C:3](Br)=[O:4].[CH:6]([NH:9][CH2:10][CH:11]([OH:24])[CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[C:19](=O)[CH2:18][CH2:17]2)([CH3:8])[CH3:7].C(Cl)Cl.C(N(CC)CC)C.[OH2:35]>C(Cl)(Cl)Cl.C1C=CC=CC=1>[CH:6]([N:9]1[C:3](=[O:4])[CH2:2][O:24][CH:11]([C:12]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[CH2:19][CH2:18][CH2:17]3)=[O:35])[CH2:10]1)([CH3:8])[CH3:7]

Participants

8

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 12800270HCID 12800270, compound

Product 1

HCID 70624490HCID 70624490, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

After adding dropwise 2.1 g. of bromoacetyl bromide to a mixture of 2.63 g. of 3-isopropylamino-1-(1-oxo-5-indanyloxy)-2-propanol, 50 ml. of methylene chloride, and 1.2 g. of triethylamine with stirring under ice-cooling, the mixture was stirred for 18 hours at room temperature and then methylene chloride was distilled off. To the residue formed were added 50 ml. of benzene and 50 ml. of water to dissolve the residue and then the benzene layer was separated from the system, washed twice each with 30 ml. of water, and dried over anhydrous magnesium sulfate. Then, benzene was distilled off and then 50 ml. of methanol having dissolved therein 0.3 g. of metallic sodium was added to the residue followed by reflux for 3 hours. Then, methanol was distilled off and to the residue were added 50 ml. of benzene and 30 ml. of water to dissolve the residue. The benzene layer formed was recovered, washed twice each with 20 ml. of water, and adsorbed on a silica gel column prepared from 50 ml. of silica gel in 100 ml. of chloroform. The residue was then eluted using ethyl acetate as the eluent and after removing the first 50 ml. of the ethyl acetate eluate emerging from the column, 100 ml. of the subsequent ethyl acetate eluate was collected and dried to provide 2.1 g. (yield 69.2%) of 4-isopropyl-5-oxo-2-(1-oxo-5-indanyloxymethyl)morpholine.

Workup

  1. additionAfter adding dropwise 2.1 g
  2. temperaturecooling
  3. distillationmethylene chloride was distilled off
  4. customTo the residue formed
  5. additionwere added 50 ml
  6. customthe benzene layer was separated from the system
  7. washwashed twice each with 30 ml
  8. dry with materialof water, and dried over anhydrous magnesium sulfate
  9. distillationThen, benzene was distilled off
  10. dissolutionof methanol having dissolved
  11. additionof metallic sodium was added to the residue
  12. temperatureby reflux for 3 hours
  13. distillationThen, methanol was distilled off and to the residue
  14. additionwere added 50 ml
  15. dissolutionof water to dissolve the residue
  16. customThe benzene layer formed
  17. customwas recovered
  18. washwashed twice each with 20 ml
  19. customprepared from 50 ml
  20. washThe residue was then eluted
  21. customafter removing the first 50 ml
  22. customof the subsequent ethyl acetate eluate was collected
  23. customdried
  24. customto provide 2.1 g

Sources & evidence

ORD record
ord-ff17e724f3c6448398ebef7bf60b82d7
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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