N-(2-Aminoethyl)isoquinoline-5-sulfonamide → N-[2-(4-Chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamide

HRID 1090584

Reaction equation

HRID 1090584 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1)(=[O:7])=[O:6].[Cl:18][C:19]1[CH:28]=[CH:27][C:22]([CH:23]=[CH:24][CH:25]=O)=[CH:21][CH:20]=1.[Na].C(OCC)(=O)C>CO>[Cl:18][C:19]1[CH:28]=[CH:27][C:22]([CH:23]=[CH:24][CH2:25][NH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]2[C:9]3[CH:10]=[CH:11][N:12]=[CH:13][C:14]=3[CH:15]=[CH:16][CH:17]=2)(=[O:7])=[O:6])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 3544N-(2-Aminoethyl)isoquinoline-5-sulfonamideHCID 8857Ethyl AcetateHCID 3794977p-ChlorocinnamaldehydeHCID 5360545Sodium

Product 1

HCID 176156N-[2-(4-Chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamideYield 71.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.01 g of N-(2-aminoethyl)-5-isoquinolinesulfonamide was dissolved in 30 ml of methanol, to the solution was added 1.60 g of p-chlorocinnamaldehyde, and the mixture was stirred for one hour at a room temperature. After an addition of 350 mg of sodium tetrahydrideborate in portions with ice cooling, the mixture was stirred for 30 minutes. After an addition of ethyl acetate, the reaction mixture was sequentially washed three times with water, and then twice with a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The mixture was filtered and evaporated to remove the solvent under a reduced pressure. A residue was purified using a silica gel column (silica gel 80 g, eluant: 5% methanol in chloroform), and resulting crystals were washed with benzene/hexane (1:1), to obtain 2.30 g of the title compound as colorless crystals.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. washthe reaction mixture was sequentially washed three times with water
  3. dry with materialtwice with a saturated sodium chloride aqueous solution, and dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customevaporated
  6. customto remove the solvent under a reduced pressure
  7. customA residue was purified
  8. customresulting crystals
  9. washwere washed with benzene/hexane (1:1)

Sources & evidence

ORD record
ord-28f2fa3e29714c79baf4ba04a2944ec3
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Linked notes

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