1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 54028169, compound

HRID 372309Notes

Reaction equation

HRID 372309 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]2[C:13]=1[CH:12]=[CH:11][C:10]([Cl:14])=[CH:9]2)=[O:4].Cl.[CH2:22]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26]Cl)[CH3:23]>>[CH3:1][NH:2][C:3]([C:5]1[N:6]([CH2:23][CH2:22][N:24]([CH2:28][CH3:29])[CH2:25][CH3:26])[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]2[C:13]=1[CH:12]=[CH:11][C:10]([Cl:14])=[CH:9]2)=[O:4]

Participants

3

Reactant 2

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 53697624HCID 53697624, compound

Product 1

HCID 54028169HCID 54028169, compound

Conditions

Temperature
70 °C

Procedure

According to the procedure described in Example 1, 28.5 g. of 5-chloro-3-phenylisoindole-1-carboxylic acid methylamide are treated with 34.5 g. of 2-diethylaminoethyl chloride hydrochloride. The mixture is heated at 70° C. for 5 hours, then cooled and poured into 4 liters of ice-water. After the addition of 200 g. of sodium chloride, the separated product is extracted with methylene chloride. The organic phase is washed with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue is digested with ether, removed by filtration and washed with ether, and there is obtained a first portion of crude 5-chloro-2-[2-(diethylamino)ethyl]-3-phenylisoindole-1-carboxylic acid methylamide having a melting point of 187°-190° C. The ethereal filtrate is extracted with 1-N sulfuric acid and the acidic extract is made alkaline at 0°-5° C. with concentrated ammonia solution. Then, the separated oil is extracted with methylene chloride and the solution dried over sodium sulfate. After evaporation, there is obtained an oil which crystallizes from ether, and is obtained as a second portion of reaction product; melting point 187°-190° C. Both portions of the reaction product are recrystallized together from ethanol, and 5-chloro-2-[2-(diethylamino)ethyl]-3-phenylisoindole-1-carboxylic acid methylamide is obtained in the form of colorless needles having a melting point of 190°-192° C.

Workup

  1. temperaturecooled
  2. additionAfter the addition of 200 g
  3. extractionof sodium chloride, the separated product is extracted with methylene chloride
  4. washThe organic phase is washed with a saturated solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customremoved by filtration
  8. washwashed with ether
  9. customthere is obtained a first portion of crude 5-chloro-2-[2-(diethylamino)ethyl]-3-phenylisoindole-1-carboxylic acid methylamide having a melting point of 187°-190° C
  10. extractionThe ethereal filtrate is extracted with 1-N sulfuric acid
  11. extractionthe acidic extract
  12. customat 0°-5° C.
  13. extractionThen, the separated oil is extracted with methylene chloride
  14. dry with materialthe solution dried over sodium sulfate
  15. customAfter evaporation
  16. customthere is obtained an oil which
  17. customcrystallizes from ether
  18. customis obtained as a second portion of reaction product
  19. customBoth portions of the reaction product are recrystallized together from ethanol

Sources & evidence

ORD record
ord-f25933d490f4421bb02567919fb02031
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

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