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

HRID 1073124Notes

Reaction equation

HRID 1073124 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+].[CH2:28]([S:32](Cl)(=[O:34])=[O:33])[CH2:29][CH2:30][CH3:31]>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:32]([CH2:28][CH2:29][CH2:30][CH3:31])(=[O:34])=[O:33])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754301-Butanesulfonyl chlorideHCID 141812122-Dipropylamino-8-(2-aminoethoxy)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 198234862-Dipropylamino-8-(2-butanesulphonamidoethoxy)-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.5 g (8.6 mmol) of 2-dipropylamino-8-(2-aminoethoxy)-1,2,3,4-tetrahydronaphthalene and 2.4 g (17.2 mmol) of potassium carbonate were initially introduced into 40 ml of toluene. 1.5 g (9.5 mmol) of butanesulphonyl chloride were added dropwise, and the mixture was then stirred for a further 2 h at room temperature. The mixture was then filtered and evaporated in a rotary evaporator. After chromatography on silica gel 60, 40-63 μm, using diisopropyl ether/ethanol, 3:2, the product was recrystallized from petroleum ether.

Workup

  1. filtrationThe mixture was then filtered
  2. customevaporated in a rotary evaporator
  3. customthe product was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-1def8de466b94a9fadc5cd9576682008
Source dataset
uspto-grants-1990_11
Patent number
US04968679

Reaction notes

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