Hexylamine → HCID 14326807, compound

HRID 2291955Notes

Reaction equation

HRID 2291955 reaction equation
[CH2:1]([N:3]([CH2:17][CH2:18]OS(C1C=CC(C)=CC=1)(=O)=O)[S:4]([C:7]1[C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1)(=[O:6])=[O:5])[CH3:2].[CH2:30]([NH2:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>ClCCl>[CH2:1]([N:3]([CH2:17][CH2:18][NH:36][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[S:4]([C:7]1[C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1)(=[O:5])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 8102HexylamineHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 21278399HCID 21278399, compound

Product 1

HCID 14326807HCID 14326807, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

To 3.96 g of the thus obtained N-ethyl-N-(2-p-toluenesulfonyloxyethyl)-5-isoquinolinesulfonamide were added 1.25 g of hexylamine, 1.14 g of potassium carbonate and 20 ml of dioxane. The mixture thus obtained was heated in a pressure vessel at 110° C. for 72 hours, and then the dioxane was removed under reduced pressure to obtain a crude product. Then, 60 ml of dichloromethane was added to the crude product, and the mixture thus obtained was washed with 30 ml of water and dried with anhydrous magnesium sulfate. The dichloromethane was removed under reduced pressure to obtain a residue. The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C-200, solvent: a 5% methanol solution in chloroform) to obtain 2.50 g of N-ethyl-N-(2-hexylaminoethyl)-5-isoquinolinesulfonamide [Compound (28)]. Compound (28) was analyzed to give the following data.

Workup

  1. customThe mixture thus obtained
  2. customthe dioxane was removed under reduced pressure
  3. customto obtain a crude product
  4. customthe mixture thus obtained
  5. washwas washed with 30 ml of water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe dichloromethane was removed under reduced pressure
  8. customto obtain a residue
  9. customThe residue thus obtained
  10. customwas subjected to purification by silica gel column chromatography (Wacogel C-200, solvent

Sources & evidence

ORD record
ord-674926bfe8154029bf20b4d6e0550a84
Source dataset
uspto-grants-1989_01
Patent number
US04798897

Reaction notes

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