Hydrochloric Acid → 2H-Isoindole-1-carboxylic acid, 5-chloro-2-(2-(diethylamino)ethyl)-3-phenyl-, ethyl ester, monohydrochloride
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23](=O)[N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[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].B.Cl>O1CCCC1>[ClH:15].[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 0.82 g. of 5-chloro-2[(diethylcarbamoyl)methyl]-3-phenylisoindole-1-carboxylic acid ethyl ester in 5 ml. of tetrahydrofuran is added dropwise under argon at room temperature to 3 ml. of a 1-M solution of borane in tetrahydrofuran. Subsequently, the mixture is boiled at reflux for 4 hours and then treated at 15°-20° C. with 0.8 ml. of 6-N hydrochloric acid. Then, the tetrahydrofuran is removed by distillation at atmospheric pressure. The residue is partitioned between 3 ml. of water and 5 ml. of ether. 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
- temperatureat reflux for 4 hours
- additiontreated at 15°-20° C. with 0.8 ml
- customThen, the tetrahydrofuran is removed by distillation at atmospheric pressure
- customThe residue is partitioned between 3 ml
- temperatureAfter cooling in an ice-bath
Sources & evidence
- ORD record
- ord-3b77d931d71844e6a7f8c31f74065781
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04090027
Reaction notes
Loading…