Hydrochloric Acid → HCID 21487254, compound

HRID 1414380Notes

Reaction equation

HRID 1414380 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[N:6]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[OH-].[Na+].Cl>C(N)(C)C.CC(C)=O.C(OCC)C>[ClH:1].[CH:15]([NH:6][CH2:2][CH2:3][O:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[N:6]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:20])[CH3:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 21487243HCID 21487243, compound

Product 1

HCID 21487254HCID 21487254, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6363IsopropylamineSolvent

Procedure

A solution of 3-(2-chloroethoxy)-2-phenyl-isoindolin-1-one in isopropylamine (120cc.) is heated in an autoclave at 120°C. for 24 hours. After cooling, the reaction mixture is poured into water (200 cc.) and 4N sodium hydroxide solution (16 cc.). The alkaline solution obtained is extracted with diethyl ether (250 cc.). The organic solution is washed with water (3 × 50 cc.) and is then extracted with 4N hydrochloric acid (18 cc.). The acid solution obtained is rendered alkaline by adding 4N sodium hydroxide solution (20 cc.) and the oily product which separates out is extracted with diethyl ether (2 × 100 cc.). The organic extracts are then dried over sodium sulphate and concentrated to dryness under reduced pressure. A product (14.2 g.), which melts at about 85°C., is obtained and is dissolved in acetone (150 cc.). A 4.03N solution of hydrogen chloride in diethyl ether (11.3 cc.) is added to the resulting solution. The product which crystallises is filtered off and then washed with acetone (10 cc.). After drying, 3-(2-isopropylaminoethoxy)-2-phenyl-isoindolin-1-one hydrochloride (11.3 g.), which melts at 184° C., is obtained.

Workup

  1. temperatureAfter cooling
  2. customThe alkaline solution obtained
  3. extractionis extracted with diethyl ether (250 cc.)
  4. washThe organic solution is washed with water (3 × 50 cc.)
  5. extractionis then extracted with 4N hydrochloric acid (18 cc.)
  6. customThe acid solution obtained
  7. extractionthe oily product which separates out is extracted with diethyl ether (2 × 100 cc.)
  8. dry with materialThe organic extracts are then dried over sodium sulphate
  9. concentrationconcentrated to dryness under reduced pressure
  10. customA product (14.2 g.), which melts at about 85°C., is obtained
  11. customThe product which crystallises
  12. filtrationis filtered off
  13. washwashed with acetone (10 cc.)
  14. customAfter drying

Sources & evidence

ORD record
ord-937c92cba1d64c009bb45b24746fbfed
Source dataset
uspto-grants-1977_01
Patent number
US04001271

Reaction notes

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