Sodium Iodide → 5-Chloro-2-[4-(diethylamino)butyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride

HRID 1973292Notes

Reaction equation

HRID 1973292 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24][CH2:25]Br)[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].[I-].[Na+].[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30]>CC(C)=O>[ClH:15].[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24][CH2:25][N:31]([CH2:32][CH3:33])[CH2:29][CH3:30])[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]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8021DiethylamineHCID 542186872-(4-Bromobutyl)-5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester

Product 1

HCID 706206645-Chloro-2-[4-(diethylamino)butyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 8.7 g. of 2-(4-bromobutyl)-5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester in 40 ml. of acetone is treated with 3.0 g. of sodium iodide and 1.6 g. of diethylamine and stirred in the dark at room temperature for 20 hours. After concentration under reduced pressure, the residue is treated at 0°-2° C. with 40 ml. of 1-N sodium hydroxide solution and then extracted with ether. The ethereal extract is immediately shaken with 40 ml. of 0.5-N hydrochloric acid and the acidic aqueous phase is made alkaline at 0°-2° C. with 1-N sodium hydroxide solution. The mixture is immediately extracted with methylene chloride and the organic phase, shielded from daylight, is dried over sodium sulfate. After concentration, the resulting oil is dissolved in ether and treated with ethereal hydrochloric acid. The crystallized hydrochloride is removed by filtration and washed with ether, and there is obtained 5-chloro-2-[4-(diethylamino)butyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride; melting point 137°-140° C. Recrystallization from methylene chloride/ether does not increase the melting point.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. additionthe residue is treated at 0°-2° C. with 40 ml
  3. extractionof 1-N sodium hydroxide solution and then extracted with ether
  4. extractionThe ethereal extract
  5. customat 0°-2° C.
  6. extractionThe mixture is immediately extracted with methylene chloride
  7. dry with materialis dried over sodium sulfate
  8. concentrationAfter concentration
  9. dissolutionthe resulting oil is dissolved in ether
  10. additiontreated with ethereal hydrochloric acid
  11. customThe crystallized hydrochloride is removed by filtration
  12. washwashed with ether

Sources & evidence

ORD record
ord-e65d86c1f33e477aa855bdf30726d035
Source dataset
uspto-grants-1976_12
Patent number
US03996374

Reaction notes

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