4-Methoxybenzenesulfonyl chloride → 2-[(N,N-Dimethylamino)methyl]-6-[4-[(4-methoxyphenyl) sulfonylamino)benzyloxy]tetralin

HRID 1242880Notes

Reaction equation

HRID 1242880 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[NH2:18][C:19]1[CH:40]=[CH:39][C:22]([CH2:23][O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[CH2:31][CH:30]([CH2:35][N:36]([CH3:38])[CH3:37])[CH2:29][CH2:28]3)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.N1C=CC=CC=1>[CH3:38][N:36]([CH2:35][CH:30]1[CH2:29][CH2:28][C:27]2[C:32](=[CH:33][CH:34]=[C:25]([O:24][CH2:23][C:22]3[CH:21]=[CH:20][C:19]([NH:18][S:14]([C:11]4[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=4)(=[O:16])=[O:15])=[CH:40][CH:39]=3)[CH:26]=2)[CH2:31]1)[CH3:37]

Participants

7

Reactant 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 219397226-(4-Aminobenzyloxy)-2-[(N,N-dimethylamino)methyl]tetralin

Product 1

HCID 210630382-[(N,N-Dimethylamino)methyl]-6-[4-[(4-methoxyphenyl) sulfonylamino)benzyloxy]tetralinYield 56%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

THF solution (1 ml) of 4-methoxybenzenesulfonyl chloride (270 mg) was added dropwise to pyridine solution (6 ml) of 6-[(4-aminobenzyl)oxy]-2-[(N,N-dimethylamino)methyl]tetralin (300 mg) under ice-cooling, which was stirred for 15 minutes. After stirring at room temperature for further 15 minutes, 10% aqueous potassium carbonate solution was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent: ethyl acetate), and recrystallized (ethyl acetate-IPE) to give the titled compound (260 mg).

Workup

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for further 15 minutes
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customrecrystallized (ethyl acetate-IPE)

Sources & evidence

ORD record
ord-390cef634ea045ffa6fa9b10500e5bdb
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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