Reaction #5828

ord-941e293f0a7c46e8b8635a04d61fecdf

Reaction equation

CI
methyl iodide
O=C([O-])[O-].[K+].[K+]
potassium carbonate
C1CCOC1.CN(C)C=O
dimethylformamide tetrahydrofuran
Cl
hydrochloric acid
CN(C(Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)CN1CCC2(CC1)OCCO2)S(=O)(=O)c1cccc2cnccc12
compound
CN(C(Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)CN1CCC2(CC1)OCCO2)S(=O)(=O)c1cccc2cnccc12
N-{2-(4,4-ethylenedioxypiperidino)-1-[p-(5-isoquinolinesulfonyloxy)benzyl]ethyl}-N-methyl-5-isoquinolinesulfonamide
→
COc1ccc(CC(CN2CCC(=O)CC2)N(C)S(=O)(=O)c2cccc3cnccc23)cc1
N-{1-(p-methoxybenzyl)-2-(4-oxopiperidino)ethyl}-N-methyl-5-isoquinolinesulfonamide

Reactants

CI
methyl iodide
O=C([O-])[O-].[K+].[K+]
potassium carbonate
C1CCOC1.CN(C)C=O
dimethylformamide tetrahydrofuran
Cl
hydrochloric acid
CN(C(Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)CN1CCC2(CC1)OCCO2)S(=O)(=O)c1cccc2cnccc12
compound
CN(C(Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)CN1CCC2(CC1)OCCO2)S(=O)(=O)c1cccc2cnccc12
N-{2-(4,4-ethylenedioxypiperidino)-1-[p-(5-isoquinolinesulfonyloxy)benzyl]ethyl}-N-methyl-5-isoquinolinesulfonamide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The amorphous compound obtained in Example 94 was subjected to alkaline hydrolysis, methylation with methyl iodide and potassium carbonate in dimethylformamide/tetrahydrofuran (1:1), and reflux with 3N hydrochloric acid, to obtain N-{1-(p-methoxybenzyl)-2-(4-oxopiperidino)ethyl}-N-methyl-5-isoquinolinesulfonamide in a colorless amorphous form.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05245034uspto-grants-1993_09