Diethylamine → HCID 70607133, compound

HRID 1863094Notes

Reaction equation

HRID 1863094 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]([C:12]1[NH:13][C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:15]2[C:20]=1[CH:19]=[CH:18][C:17]([Cl:21])=[CH:16]2)=[O:11])(=O)=O.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>CC(C)=O>[ClH:21].[CH2:28]([N:30]([CH2:31][CH3:32])[CH2:6][CH2:7][CH2:8][O:9][C:10]([C:12]1[NH:13][C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:15]2[C:20]=1[CH:19]=[CH:18][C:17]([Cl:21])=[CH:16]2)=[O:11])[CH3:29]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 53827968HCID 53827968, compound

Product 1

HCID 70607133HCID 70607133, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 0.82 g. of 5-chloro-3-phenylisoindole-1-carboxylic acid 3-[(methylsulfonyl)oxy]propyl ester in 8 ml. of acetone is treated with 2 ml. of diethylamine and the mixture is boiled at reflux for 5 hours. The mixture is then concentrated to dryness under reduced pressure and the residue partitioned between 15 ml. of water and 15 ml. of diethyl ether. The ethereal phase is treated with 6 ml. of 0.5-N hydrochloric acid and the mixture shaken well. After cooling in an ice-bath, the hydrochloride which crystallizes out is removed by filtration, dried and recrystallized from methanol/diethyl ether, and there is obtained 5-chloro-3-phenylisoindole-1-carboxylic acid 3-(diethylamino)propyl ester hydrochloride having a melting point of 248°-251° 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 15 ml
  4. additionThe ethereal phase is treated with 6 ml
  5. temperatureAfter cooling in an ice-bath
  6. customthe hydrochloride which crystallizes out
  7. customis removed by filtration
  8. customdried
  9. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-768104ca29d846058261c91a743e0754
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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