N-Methylbutylamine → 2-[3-(Butylmethylamino)propyl]-5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride

HRID 1973308Notes

Reaction equation

HRID 1973308 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][NH:31][CH2:32][CH2:33][CH2:34][CH3:35]>CC(C)=O>[ClH:15].[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24][N:31]([CH2:32][CH2:33][CH2:34][CH3:35])[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

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 54315092HCID 54315092, compound

Product 1

HCID 706209342-[3-(Butylmethylamino)propyl]-5-chloro-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 N-methylbutylamine and boiled at reflux for 5 hours. The mixture is then concentrated to dryness under reduced pressure and the residue partitioned between 50 ml. of water and 50 ml. of ether. The ethereal phase is treated with 30 ml. of 0.5-N hydrochloric acid and the mixture thoroughly shaken. After cooling in an ice-bath, the crystallized hydrochloride is removed by filtration under vacuum, dried and recrystallized from methylene chloride/ether, and there is obtained 2-[3-(butylmethylamino)propyl]-5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride having a melting point of 98°-101° C. (decomposition).

Workup

  1. temperatureat reflux for 5 hours
  2. concentrationThe mixture is then concentrated to dryness under reduced pressure
  3. customthe residue partitioned between 50 ml
  4. additionThe ethereal phase is treated with 30 ml
  5. temperatureAfter cooling in an ice-bath
  6. customthe crystallized hydrochloride is removed by filtration under vacuum
  7. customdried
  8. customrecrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-3e09614d86b542c29414d0f2db8db5ba
Source dataset
uspto-grants-1976_12
Patent number
US03996374

Reaction notes

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