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

HRID 728088Notes

Reaction equation

HRID 728088 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:15][CH2:16][NH2:17])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH3:27][S:28]([Cl:31])(=[O:30])=[O:29]>C(Cl)Cl>[ClH:31].[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:15][CH2:16][NH:17][S:28]([CH3:27])(=[O:30])=[O:29])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 141812202-Dipropylamino-8-(2-aminoethyl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 198234662-Dipropylamino-8-(2-methanesulphonamido-ethyl)-1,2,3,4-tetrahydronaphthalene hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.2 g (4.4 mmol) of 2-dipropylamino-8-(2-aminoethyl)-1,2,3,4-tetrahydronaphthalene and 1.21 g (8.8 mmol) of potassium carbonate were initially introduced into 20 ml of methylene chloride. 550 mg (4.8 mmol) of methanesulphonyl chloride were then added dropwise at 25° C. The mixture was stirred overnight at room temperature. The mixture was then filtered, and the filtrate was washed once with water, dried over sodium sulphate and evaporated. Diethyl ether was added to the residue, methylene chloride was added until everything was dissolved, and the hydrochloride was precipitated using ethereal hydrochloric acid. The product was filtered off under suction and dried at 40° C. in a high vacuum.

Workup

  1. filtrationThe mixture was then filtered
  2. washthe filtrate was washed once with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. additionDiethyl ether was added to the residue, methylene chloride
  6. additionwas added until everything
  7. dissolutionwas dissolved
  8. customthe hydrochloride was precipitated
  9. filtrationThe product was filtered off under suction
  10. customdried at 40° C. in a high vacuum

Sources & evidence

ORD record
ord-b2464aa4bd5f4e8086f3084223256e5b
Source dataset
uspto-grants-1991_09
Patent number
US05047422

Reaction notes

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