Monomethylamine methanol → 4-aminomethyl-N-(4-dipropylaminobutyl)benzenesulfonamide

HRID 1173861Notes

Reaction equation

HRID 1173861 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])(=[O:21])=[O:20])=[CH:15][CH:14]=1.CN.CO>>[NH2:3][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])(=[O:20])=[O:21])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 57454252Monomethylamine methanolHCID 669411664-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)-N-(4-dipropylaminobutyl)benzenesulfonamide

Product 1

HCID 230792764-aminomethyl-N-(4-dipropylaminobutyl)benzenesulfonamideYield 98.4%

Procedure

The compound (160 mg) obtained in Example 24-3 was added with 2.0 ml of a 40% methylamine/methanol solution (manufactured by Tokyo Kasei Kogyo Co., Ltd.), followed by stirring at room temperature for 40 hours. After completion of the reaction, the solvent was distilled off and the residue was subjected to extraction by the addition of a 1 mol/l sodium hydroxide aqueous solution and chloroform. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off, thereby obtaining the subject compound (114 mg) as a colorless viscous liquid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. extractionthe residue was subjected to extraction by the addition of a 1 mol/l sodium hydroxide aqueous solution and chloroform
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-03f8a3dae49546378913422834efa429
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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