Potassium Carbonate → 2H-Isoindole-1-carboxylic acid, 5-chloro-2-(2-(diethylamino)ethyl)-3-phenyl-, ethyl ester, monohydrochloride

HRID 372310Notes

Reaction equation

HRID 372310 reaction equation
Cl.[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6][Cl:7])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:16]([O:18][C:19]([C:21]1[NH:22][C:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:24]2[C:29]=1[CH:28]=[CH:27][C:26]([Cl:30])=[CH:25]2)=[O:20])[CH3:17]>CS(C)=O>[ClH:7].[CH2:16]([O:18][C:19]([C:21]1[N:22]([CH2:3][CH2:2][N:4]([CH2:8][CH3:9])[CH2:5][CH3:6])[C:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:24]2[C:29]=1[CH:28]=[CH:27][C:26]([Cl:30])=[CH:25]2)=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 54174784Ethyl 5-chloro-3-phenyl-2H-isoindole-1-carboxylate

Product 1

HCID 30458932H-Isoindole-1-carboxylic acid, 5-chloro-2-(2-(diethylamino)ethyl)-3-phenyl-, ethyl ester, monohydrochloride

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5.2 g. of 2-diethylaminoethyl chloride hydrochloride in 35 ml. of dimethylsulfoxide is treated with 8.3 g. of finely ground dry potassium carbonate and stirred at room temperature for 15 minutes. Then, there are added thereto 3.0 g. of 5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester; the mixture is stirred intensively for 18 hours under an atmosphere of nitrogen at room temperature and subsequently poured onto 80 ml. of ice-water. After the addition of 5 g. of sodium chloride, the separated oil is immediately extracted with ether, and the extract concentrated to about 30 ml. and treated with 30 ml. of 0.5-N hydrochloric acid. The mixture is thoroughly shaken and cooled in an ice-bath. The crystallized hydrochloride is isolated and purified in an analogous manner to that given in Example 1, and there is obtained 5-chloro-2-[2-(diethylamino)ethyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride having a melting point of 248°-250° C. (decomposition).

Workup

  1. additionThen, there are added
  2. additionsubsequently poured onto 80 ml
  3. additionAfter the addition of 5 g
  4. extractionof sodium chloride, the separated oil is immediately extracted with ether
  5. concentrationthe extract concentrated to about 30 ml
  6. additionand treated with 30 ml
  7. stirringThe mixture is thoroughly shaken
  8. temperaturecooled in an ice-bath

Sources & evidence

ORD record
ord-8579a10e736a4a81a8d07fa3b6ca27f5
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

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