Chloroform → HCID 22180271, compound

HRID 1836837Notes

Reaction equation

HRID 1836837 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[C:22]3[C:17]([CH2:18][CH2:19][NH:20][C:21]3=[O:24])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:25]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:23]([Cl:25])=[C:22]3[C:17]([CH2:18][CH2:19][NH:20][C:21]3=[O:24])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6547AzobisisobutyronitrileHCID 31398ChlorosuccinimideHCID 107352707-(4-Tert-butoxycarbonyl-piperazin-1-yl)-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 22180271HCID 22180271, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

The compound (6.63 g) prepared in step (a) of Example 125 was dissolved in carbon tetrachloride (200 ml). N-Chlorosuccinimide (3.47 g) and AIBN (0.66 g) were added to the solution, and the mixture was heated at 90° C. with stirring for one hr. The temperature of the reaction solution was returned to room temperature. Chloroform was then added to the reaction solution, and the mixture was washed with water, followed by drying over anhydrous MgSO4. The solvent was then removed by distillation under the reduced pressure. The residue was crudely purified by column chromatography on silica gel (ethyl acetate). The solvent was removed by distillation under the reduced pressure. Chloroform was added to the residue, and the precipitated crystal was collected by filtration (and washed with diethyl ether) to give 7-(4-tert-butoxycarbonyl-piperazin-1-yl)-8-chloro-3,4-dihydro-2H-isoquinolin-1-one (0.89 g).

Workup

  1. customwas returned to room temperature
  2. washthe mixture was washed with water
  3. dry with materialby drying over anhydrous MgSO4
  4. customThe solvent was then removed by distillation under the reduced pressure
  5. customThe residue was crudely purified by column chromatography on silica gel (ethyl acetate)
  6. customThe solvent was removed by distillation under the reduced pressure
  7. additionChloroform was added to the residue
  8. filtrationthe precipitated crystal was collected by filtration (and washed with diethyl ether)

Sources & evidence

ORD record
ord-c0815b21bd1f4737b93fa5cfb830de8f
Source dataset
uspto-grants-2004_08
Patent number
US06777414B1

Reaction notes

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