Succinimide → HCID 68136841, compound

HRID 268440Notes

Reaction equation

HRID 268440 reaction equation
[O:1]1[CH2:29][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13][C@@H:12]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][CH:6]=1.[C:30]1(=[O:36])[NH:34][C:33](=[O:35])[CH2:32][CH2:31]1>N1CCCCC1.C(O)C>[C:33]1(=[O:35])[N:34]([CH2:29][CH:2]([OH:1])[CH2:3][O:4][C:5]2[CH:6]=[CH:7][C:8]([C@@H:11]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[CH2:14][CH2:13][C@@H:12]3[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:9][CH:10]=2)[C:30](=[O:36])[CH2:31][CH2:32]1

Participants

5

Reactant 2

HCID 11439SuccinimideHCID 54273062HCID 54273062, compound

Product 1

HCID 68136841HCID 68136841, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.0 g. of cis-1-[p-(2,3-epoxypropoxy)phenyl]-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalene, 0.80 g. of succinimide and 4 drops of piperidine in 100 ml. of absolute ethanol is heated under reflux for 17 hours. The resulting mixture is concentrated to approximately one-third volume by distillation under reduced pressure and the residue is diluted with water. The mixture so obtained is extracted with methylene chloride and the methylene chloride extract is washed with water and saturated sodium chloride solution before being evaporated to dryness. The residue is recrystallized from aqueous alcohol to yield cis-1-[p-(3-succinimido-2-hydroxy-propoxy)phenyl]-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalene. The latter compound is then heated under reflux for 20 hours with a solution of 16 g. of sodium hydroxide in 320 ml. of ethanol. The resulting product is concentrated by distillation under reduced pressure and the residue is extracted with a mixture of methylene chloride and water. The methylene chloride solution is separated, washed with water, and taken to dryness. Hydrogen chloride is bubbled through a solution of the residue in ether. The solid which separates is isolated by filtration, and dried. There is thus obtained cis-1-[p-(3-amino-2-hydroxy-propoxy)phenyl]-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride. The corresponding free base is obtained by dissolving the hydrochloride in methylene chloride, washing the resulting solution with an aqueous sodium bicarbonate solution, and evaporating the methylene chloride solution to dryness.

Workup

  1. additionA mixture of 3.0 g
  2. temperatureunder reflux for 17 hours
  3. concentrationThe resulting mixture is concentrated to approximately one-third volume by distillation under reduced pressure
  4. additionthe residue is diluted with water
  5. customThe mixture so obtained
  6. extractionis extracted with methylene chloride
  7. extractionthe methylene chloride extract
  8. washis washed with water and saturated sodium chloride solution
  9. custombefore being evaporated to dryness
  10. customThe residue is recrystallized from aqueous alcohol

Sources & evidence

ORD record
ord-436b5f5519534f8fae4914ac2b8be72f
Source dataset
uspto-grants-1976_03
Patent number
US03947520

Reaction notes

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