Benzo-1,3-dioxole-5-methylamine → HCID 15225104, compound

HRID 1742588Notes

Reaction equation

HRID 1742588 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][NH:13][S:14]([C:17]2[C:18]3[CH:19]=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])(=O)=O)=CC=1.[CH2:28]1[O:38][C:37]2[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][C:30]=2[O:29]1>O1CCCC1>[CH2:28]1[O:38][C:37]2[CH:36]=[CH:35][C:32]([CH2:33][NH:34][CH2:11][CH2:12][NH:13][S:14]([C:17]3[C:18]4[CH:19]=[CH:20][N:21]=[CH:22][C:23]=4[CH:24]=[CH:25][CH:26]=3)(=[O:15])=[O:16])=[CH:31][C:30]=2[O:29]1

Participants

4

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 14774003HCID 14774003, compound

Product 1

HCID 15225104HCID 15225104, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4.06 g of the thus obtained N-(2-paratoluenesulfonyloxyethyl)-5-isoquinolinesulfonamide was added 40 ml of tetrahydrofuran containing 4.53 g of 3,4-methylenedioxybenzylamine. The resultant mixture was heated in a sealed vessel at 100° C. for 17 hours and then, the solvent was removed by distillation under reduced pressure to obtain a residue. The thus obtained residue was subjected to purification by means of a column for chromatography packed with 200 g of silica gel (Wacogel C-200, manufactured by Wako Pure Chemical Industries, Ltd., Japan) using, as an eluent, a mixture of methanol and chloroform (0.5% methanol) to obtain 1.84 g of N-[2-(3,4-methylenedioxybenzylamino)ethyl]-5-isoquinolinesulfonamide (3) (yield: 48%).

Workup

  1. customthe solvent was removed by distillation under reduced pressure
  2. customto obtain a residue
  3. customThe thus obtained residue was subjected to purification by means of a column for chromatography
  4. additiona mixture of methanol and chloroform (0.5% methanol)

Sources & evidence

ORD record
ord-5f9ccb3e2c7a46f4b8c3c48f5984710c
Source dataset
uspto-grants-1994_08
Patent number
US05340811

Reaction notes

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