Amantadine → HCID 20544735, compound

HRID 2286957Notes

Reaction equation

HRID 2286957 reaction equation
C(Cl)(Cl)Cl.[CH2:5]1[CH:10]2[CH2:11][C:12]3([NH2:15])[CH2:14][CH:8]([CH2:9]2)[CH2:7][CH:6]1[CH2:13]3.[O:16]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26](Cl)=[O:27])[C:20]=2[O:19][CH2:18][CH2:17]1>O>[C:12]12([NH:15][C:26]([C:25]3[C:20]4[O:19][CH2:18][CH2:17][O:16][C:21]=4[CH:22]=[CH:23][CH:24]=3)=[O:27])[CH2:14][CH:8]3[CH2:9][CH:10]([CH2:5][CH:6]([CH2:7]3)[CH2:13]1)[CH2:11]2

Participants

5

Reactant 3

HCID 2130AmantadineHCID 6212ChloroformHCID 27950312,3-Dihydro-1,4-benzodioxine-5-carbonyl chloride

Product 1

HCID 20544735HCID 20544735, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 ml of chloroform and 37.5 g of adamantamine were introduced into a balloon flask provided with an agitator and a thermometer, and then 50 g of 1,4-benzodioxane-5-carbonyl chloride was added in portions at a temperature of from 5°-10° C. After agitation at ambient temperature 1500 ml of water was added and then chloroform was removed under vacuum. The base which was precipitated by ammonia was extracted by means of methylene chloride. After removal of the solvent the residue was dissolved in hydrochloric ethanol. The crystals formed by cooling were dried off, washed and then dried. 20 g of N-(1-adamantyl)-1,4-benzodioxane-5-carboxamide was produced (M.P.: 137° C.; yield: 25%).

Workup

  1. customprovided with an agitator
  2. customchloroform was removed under vacuum
  3. customThe base which was precipitated by ammonia
  4. extractionwas extracted by means of methylene chloride
  5. customAfter removal of the solvent the residue
  6. dissolutionwas dissolved in hydrochloric ethanol
  7. customThe crystals formed
  8. temperatureby cooling
  9. customwere dried off
  10. washwashed
  11. customdried

Sources & evidence

ORD record
ord-c39194bbbe5f431fadbbe601ed2690a5
Source dataset
uspto-grants-1981_05
Patent number
US04268512

Reaction notes

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