Isopropylamine → HCID 86734350, compound

HRID 1414382Notes

Reaction equation

HRID 1414382 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([NH2:27])(C)C.[OH-].[Na+].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>C1(C)C=CC=CC=1.C(O)(C)C.C(OCC)C.O>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[CH:31]([CH:2]([NH2:27])[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:32])[CH3:30]

Participants

9

Reactant 4

HCID 6363IsopropylamineHCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 21487246HCID 21487246, compound

Product 1

HCID 86734350HCID 86734350, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 3-(5-chloropentyloxy)-2-phenyl-isoindolin-1-one (31.6 g.) and isopropylamine (83 cc.) in toluene (50 cc.) is heated in an autoclave at 140°C. for 48 hours. After cooling, the reaction mixture is poured into water (200 cc.) and diethyl ether (200 cc.). The organic phase is separated. The aqueous solution is washed with diethyl ether (2 × 55 cc.). The organic solutions obtained are combined and washed with water (5 × 25 cc.) and are then extracted with 4N hydrochloric acid (3 × 35 cc.). The acid solutions obtained are combined and rendered alkaline by adding 10N sodium hydroxide solution (45 cc.). The resulting insoluble oil is extracted with methylene chloride (3 × 80 cc.) and the organic solution obtained is dried over sodium sulphate and concentrated to dryness under reduced pressure. An oil (30 g.) is obtained and is dissolved in isopropanol (250 cc.). Fumaric acid (9.3 g.) is added to the solution and the mixture is then heated to the boiling point. A slight amount of insoluble matter is removed by carrying out a hot filtration. The product which crystallises on cooling is filtered off and then washed with isopropanol (50 cc.) and acetone (50 cc.). After drying, 3-(5-isopropyl-aminopentyloxy)-2-phenyl-isoindolin-1-one hydrogen fumarate (30.6 g.), which melts at 150°C., is obtained.

Workup

  1. temperatureAfter cooling
  2. customThe organic phase is separated
  3. washThe aqueous solution is washed with diethyl ether (2 × 55 cc.)
  4. customThe organic solutions obtained
  5. washwashed with water (5 × 25 cc.)
  6. extractionare then extracted with 4N hydrochloric acid (3 × 35 cc.)
  7. customThe acid solutions obtained
  8. extractionThe resulting insoluble oil is extracted with methylene chloride (3 × 80 cc.)
  9. customthe organic solution obtained
  10. dry with materialis dried over sodium sulphate
  11. concentrationconcentrated to dryness under reduced pressure
  12. customAn oil (30 g.) is obtained
  13. temperaturethe mixture is then heated to the boiling point
  14. customA slight amount of insoluble matter is removed
  15. filtrationa hot filtration
  16. customThe product which crystallises
  17. temperatureon cooling
  18. filtrationis filtered off
  19. washwashed with isopropanol (50 cc.) and acetone (50 cc.)
  20. customAfter drying

Sources & evidence

ORD record
ord-b395d123deab48b8a167e9bf00efa0e3
Source dataset
uspto-grants-1977_01
Patent number
US04001271

Reaction notes

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