Homoveratrylamine → HCID 19007105, compound

HRID 1742593Notes

Reaction equation

HRID 1742593 reaction equation
C1(C)C=CC(S(O[CH:11]([CH3:28])[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.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[CH2:35][CH2:36][NH2:37]>O1CCCC1>[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[CH2:35][CH2:36][NH:37][CH:11]([CH3:28])[CH2:12][NH:13][S:14]([C:17]1[C:18]2[CH:19]=[CH:20][CH:21]=[N:22][C:23]=2[C:24]([Cl:27])=[CH:25][CH:26]=1)(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 86748084HCID 86748084, compound

Product 1

HCID 19007105HCID 19007105, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

50 ml of a tetrahydrofuran solution containing 4.58 g of N-(2-paratoluenesulfonyloxypropyl)-8-chloro-5-quinolinesulfonamide and 4.95 g of 3,4-dimethoxyphenethylamine was heated at 70° C. for 8 hours in a sealed vessel. Then, the solvent was removed by distillation under reduced pressure to obtain a residue. The thus obtained residue was subjected to purification by silica gel column chromatography [Wacogel C-200, 200 g; solvent: a mixture of methanol and chloroform (5% methanol)] to obtain 2.37 g of N-[2-(3,4-dimethoxyphenethylamino)-2-methylethyl]-8-chloro-5-quinolinesulfonamide (60) (yield: 51%).

Workup

  1. customThen, the solvent was removed by distillation under reduced pressure
  2. customto obtain a residue
  3. customThe thus obtained residue was subjected to purification by silica gel column chromatography [Wacogel C-200, 200 g
  4. additionsolvent: a mixture of methanol and chloroform (5% methanol)]

Sources & evidence

ORD record
ord-266bcdc111dc4dbbab30a9fe89bcbbc8
Source dataset
uspto-grants-1994_08
Patent number
US05340811

Reaction notes

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