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Potassium Carbonate → 2-Dipropylamino-8-(2-methanesulphonamido-ethoxy)-1,2,3,4-tetrahydronaphthalene

HRID 728081
Notes
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Reaction equation

HRID 728081 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([O:15][CH2:16][CH2:17][NH2:18])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(OC(C)C)(C)C.C(O)C>C1(C)C=CC=CC=1>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([O:15][CH2:16][CH2:17][NH:18][S:29]([CH3:28])(=[O:31])=[O:30])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:20][CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 141812122-Dipropylamino-8-(2-aminoethoxy)-1,2,3,4-tetrahydronaphthaleneHCID 23358034Diisopropyl ether ethanol

Product 1

HCID 141812132-Dipropylamino-8-(2-methanesulphonamido-ethoxy)-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.45 g (5 mmol) of 2-dipropylamino-8-(2-aminoethoxy)-1,2,3,4-tetrahydronaphthalene and 1.38 g (10 mmol) of potassium carbonate were initially introduced into 20 ml of toluene. 0.63 g (5.5 mmol) of methanesulphonyl chloride was then added dropwise, and the mixture was subsequently stirred for 3 h at room temperature. The mixture was then filtered and evaporated. The residue obtained was stirred with petroleum ether and filtered off under suction. The product, obtained by chromatography over silica gel 60, 40-63 μm, using diisopropyl ether/ethanol, 3:2, was recrystallized from petroleum ether with activated charcoal.

Workup

  1. filtrationThe mixture was then filtered
  2. customevaporated
  3. customThe residue obtained
  4. filtrationfiltered off under suction
  5. customThe product, obtained by chromatography over silica gel 60, 40-63 μm
  6. customwas recrystallized from petroleum ether with activated charcoal

Sources & evidence

ORD record
ord-fc3bf5a865a345cdbc51a83f778d2b77
Source dataset
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05047422

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes