Water → HCID 54357522, compound

HRID 1585542Notes

Reaction equation

HRID 1585542 reaction equation
Br[CH2:2][C:3]([NH:5][CH2:6][C@@H:7]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)[NH2:8])=[O:4].C(=O)([O-])[O-].[K+].[K+].O.ClCCl>CN(C)C=O>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][C@@H:7]2[CH2:6][NH:5][C:3](=[O:4])[CH2:2][NH:8]2)=[CH:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 53896521HCID 53896521, compound

Product 1

HCID 54357522HCID 54357522, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (1R)-N2 -(bromoacetyl)-1-(1H-indol-3-ylmethyl)-1,2-ethanediamine (3.30 g) in dimethylformamide (70 ml) was added potassium carbonate (3.30 g) at room temperature. The reaction mixture was stirred at 110° C. for 1 hour and 20 minutes. After cooling to room temperature, water and dichloromethane were added into the mixture, and the organic layer was separated. The aqueous layer was extracted successively with dichloromethane several times and a mixed solvent of ethyl acetate and methanol (10:1). The extracts were combined and dried over magnesium sulfate, and concentrated under reduced pressure to give (5R)-5-(1H-indol-3-ylmethyl)piperazin-2-one (2.47 g) as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted successively with dichloromethane several times
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e8a1e3b2c2441dda7c0083b383aa2fc
Source dataset
uspto-grants-1999_08
Patent number
US05939413

Reaction notes

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