Hydrochloric Acid → HCID 19095879, compound

HRID 486772Notes

Reaction equation

HRID 486772 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H-].[Na+].[CH2:17]([N:24]1[CH2:28][CH:27](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:26][C:25]1=[O:40])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.[CH3:42]N(C=O)C>O>[CH2:17]([N:24]1[C:25](=[O:40])[CH2:26][CH:27]([CH2:42][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[C:2]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:28]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylateHCID 19095951HCID 19095951, compound

Product 1

HCID 19095879HCID 19095879, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 66.2 g of ethyl indole-2-carboxylate in 350 ml of DMF was added to a suspension of 12 g of sodium hydride (80% dispersion in mineral oil) in 80 ml of DMF. After stirring for 0.5 hour under a nitrogen atmosphere the solution obtained was treated with a solution of 115 g of 1-benzyl-4-(p-toluenesulphonyloxy)-2-pyrrolidinone in 500 ml of DMF. After completion of the addition the mixture was heated to 60° C. for 0.75 hour and then at 70° C. for 1 hour. The solution obtained was cooled in an ice bath and treated with water and 2M hydrochloric acid. After stirring for 15 minutes the precipitate formed was filtered off and dried to give 96.2 g of ethyl 1-[(1-benzyl-5-oxo-3-pyrrolidinyl)methyl]-2-indolecarboxylate of melting point 93°-94° C.

Workup

  1. customobtained
  2. additionAfter completion of the addition the mixture
  3. waitat 70° C. for 1 hour
  4. customThe solution obtained
  5. temperaturewas cooled in an ice bath
  6. stirringAfter stirring for 15 minutes the precipitate
  7. customformed
  8. filtrationwas filtered off
  9. customdried

Sources & evidence

ORD record
ord-9f9f590e9350467db8422dc5310a736d
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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