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

HRID 1973309Notes

Reaction equation

HRID 1973309 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24][N:25]([CH2:29][CH3:30])[C:26](=O)[CH3:27])[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>O1CCCC1>[ClH:15].[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24][N:25]([CH2:29][CH3:30])[CH2:26][CH3:27])[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 6331BoraneHCID 53716510HCID 53716510, compound

Product 1

HCID 30458952H-Isoindole-1-carboxylic acid, 5-chloro-2-(3-(diethylamino)propyl)-3-phenyl-, ethyl ester, monohydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.84 g. of 2-[3-(N-ethylacetamido)propyl]-5-chloro-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 heated at reflux for 4 hours, then treated at 15°-20° C. with 0.8 ml. of 6-N hydrochloric acid and the tetrahydrofuran is removed by distillation at atmospheric pressure. The residue is partitioned between 3 ml. of water and 5 ml. of ether and cooled in an ice-bath. The crystallized hydrochloride is isolated and purified in a manner analogous to that described in Example 5, and there is obtained 5-chloro-2-[3-(diethylamino)-propyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride having a melting point of 203°-206° C. (decomposition).

Workup

  1. temperatureSubsequently, the mixture is heated
  2. temperatureat reflux for 4 hours
  3. additiontreated at 15°-20° C. with 0.8 ml
  4. customof 6-N hydrochloric acid and the tetrahydrofuran is removed by distillation at atmospheric pressure
  5. customThe residue is partitioned between 3 ml
  6. temperatureof ether and cooled in an ice-bath

Sources & evidence

ORD record
ord-e94ded1682fa49a2b3edd97eb1201583
Source dataset
uspto-grants-1976_12
Patent number
US03996374

Reaction notes

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