1-Bromo-3-chloropropane → 8-(3-chloro-propoxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 506643Notes

Reaction equation

HRID 506643 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:6]3=[CH:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][Cl:26]>CC(=O)CC>[Cl:26][CH2:25][CH2:24][CH2:23][O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:6]3=[CH:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 684650438-hydroxy-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Product 1

HCID 684653958-(3-chloro-propoxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The suspension consistent of 0.5 g (2.4 mmol) 8-hydroxy-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 1, intermediate a), 0.41 g (2.6 mmol) potassium carbonate and 0.29 ml (0.47 g, 3.0 mmol) 1-bromo-3-chloropropane in 12 ml 2-butanone was heated under reflux for 64 hours. The reaction mixture was evaporated to dryness to give a light brown solid containing the desired product together with some starting material (0.58 g, 55%). This mixture was used in the next step without further purification.

Workup

  1. temperatureunder reflux for 64 hours
  2. customThe reaction mixture was evaporated to dryness
  3. customto give a light brown solid

Sources & evidence

ORD record
ord-ad2f0515b27841e68f2d3bc6c67ea3f9
Source dataset
uspto-grants-2010_08
Patent number
US07786109B2

Reaction notes

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