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

HRID 2351474Notes

Reaction equation

HRID 2351474 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]

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-805837dbc3124ebb9c3b37c0a24a4b54
Source dataset
uspto-grants-1989_10
Patent number
US04873262

Reaction notes

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