Bis(2-Methoxyethyl)amine → 5-Chloro-2-{3-[bis(methoxyethyl)amino]propyl}-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride

HRID 372333Notes

Reaction equation

HRID 372333 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24]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].[CH3:30][O:31][CH2:32][CH2:33][NH:34][CH2:35][CH2:36][O:37][CH3:38]>CC(C)=O>[ClH:15].[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24][N:34]([CH2:35][CH2:36][O:37][CH3:38])[CH2:33][CH2:32][O:31][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 2383Bis(2-Methoxyethyl)amineHCID 54315092HCID 54315092, compound

Product 1

HCID 706208515-Chloro-2-{3-[bis(methoxyethyl)amino]propyl}-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4.36 g. of 5-chloro-2-{3-[(methylsulfonyl)oxy]propyl}-3-phenylisoindole-1-carboxylic acid ethyl ester in 40 ml. of acetone is treated with 10 ml. of bis-(2-methoxyethyl)amine and boiled at reflux for 17 hours. The mixture is then concentrated to dryness under reduced pressure and the residue taken up in ether. After acidification with ethereal hydrochloric acid, the crystallized hydrochloride is removed by filtration under vacuum, dried and recrystallized from methylene chloride/ether, and there is obtained 5-chloro-2-{3-[bis(methoxyethyl)amino]propyl}-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride; melting point 120°-122° C.

Workup

  1. temperatureat reflux for 17 hours
  2. concentrationThe mixture is then concentrated to dryness under reduced pressure
  3. customAfter acidification with ethereal hydrochloric acid, the crystallized hydrochloride is removed by filtration under vacuum
  4. customdried
  5. customrecrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-5c1ec21b3f41498589488bc7cbea6cba
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

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