Benzo-1,3-dioxole-5-methylamine → HCID 19007128, compound

HRID 1742590Notes

Reaction equation

HRID 1742590 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][CH:21]=[N:22][C:23]=3[C:24]([Cl:27])=[CH:25][CH:26]=2)(=[O:16])=[O:15])(=O)=O)=CC=1.[CH2:29]1[O:39][C:38]2[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][C:31]=2[O:30]1>O1CCCC1>[CH2:29]1[O:39][C:38]2[CH:37]=[CH:36][C:33]([CH2:34][NH:35][CH2:11][CH2:12][NH:13][S:14]([C:17]3[C:18]4[CH:19]=[CH:20][CH:21]=[N:22][C:23]=4[C:24]([Cl:27])=[CH:25][CH:26]=3)(=[O:15])=[O:16])=[CH:32][C:31]=2[O:30]1

Participants

4

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 86748083HCID 86748083, compound

Product 1

HCID 19007128HCID 19007128, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.32 g of N-(2-paratoluenesulfonyloxyethyl)-8-chloro-5-quinolinesulfonamide was reacted with 30 ml of a tetrahydrofuran solution containing 3.41 g of 3,4-methylenedioxybenzylamine in a sealed vessel at 70° C. for 17 hours, and 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 (5% methanol) to thereby obtain 1.80 g of N-[2-(3,4-methylenedioxybenzylamino)ethyl]-8-chloro-5-quinolinesulfonamide (13) (yield: 57%)

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 (5% methanol)

Sources & evidence

ORD record
ord-9457a23838be4738977b87613d898435
Source dataset
uspto-grants-1994_08
Patent number
US05340811

Reaction notes

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