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

HRID 1679057Notes

Reaction equation

HRID 1679057 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23]OS(C)(=O)=O)[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2].[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30]>CS(C)=O>[ClH:15].[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][N:31]([CH2:32][CH3:33])[CH2:29][CH3:30])[C:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 536910545-Chloro-2-{2-[(methylsulfonyl)oxy]ethyl}-3-phenylisoindole-1-carboxylic acid ethyl ester

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 0.84 g. of 5-chloro-2-{2-[(methylsulfonyl)oxy]ethyl}-3-phenylisoindole-1-carboxylic acid ethyl ester in 5 ml. of dimethylsulfoxide is treated with 5 ml. of diethylamine and boiled at reflux for 17 hours under exclusion of light. The excess diethylamine is then evaporated under reduced pressure and the resulting solution poured into 50 ml. of ice-water. After the addition of 3 g. of sodium chloride, the separated, thick oil 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 oily residue is dissolved in 15 ml. of acetone, treated with 10 ml. of 0.5-N hydrochloric acid and the mixture is thoroughly shaken. After cooling in an ice-bath, the crystallized hydrochloride is isolated and purified in a manner analogous to that described in Example 1, and there is obtained 5-chloro-2-[2-(diethylamino)-ethyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride; melting point 248° -250° C. (decomposition).

Workup

  1. temperatureat reflux for 17 hours under exclusion of light
  2. customThe excess diethylamine is then evaporated under reduced pressure
  3. additionthe resulting solution poured into 50 ml
  4. additionAfter the addition of 3 g
  5. extractionof sodium chloride, the separated, thick oil is extracted with methylene chloride
  6. washThe organic phase is washed with a saturated solution of sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness under reduced pressure
  9. dissolutionThe oily residue is dissolved in 15 ml
  10. additionof acetone, treated with 10 ml
  11. temperatureAfter cooling in an ice-bath

Sources & evidence

ORD record
ord-06f3f9b6a2b04ac1a84fb530bc15fc19
Source dataset
uspto-grants-1978_03
Patent number
US04077978

Reaction notes

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