p-Bromobenzenesulfonyl chloride → HCID 18434163, compound

HRID 1636763Notes

Reaction equation

HRID 1636763 reaction equation
[CH2:1]([N:4]([CH3:18])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:1]([N:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][N:15]([S:35]([C:32]2[CH:33]=[CH:34][C:29]([Br:28])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[CH2:14][CH2:13]1)[CH3:18])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 22279367N-Methyl-6-[(piperidin-4-yl)oxy]-N-(prop-2-en-1-yl)hexan-1-amine

Product 1

HCID 18434163HCID 18434163, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 g of allyl-methyl-[6-(piperidin-4-yloxy)-hexyl]-amine (Ex. 49.1) are dissolved in 50 ml of methylene chloride and treated with 5.3 ml of Hunig Base (di-isopropyl-ethylamine) and 1.9 g of 4-bromo-phenylsulphonyl chloride. The reaction mixture is stirred at room temperature for 3 hours, treated with aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. The organic phases are washed with saturated sodium chloride solution, dried and concentrated. The brown oil is purified on silica gel with ethyl acetate/methanol (9:1). There are obtained 2.6 g of allyl-[6-[1-(4-bromo-phenylsulphonyl)-piperidin-4-yloxy]-hexyl]-methyl-amine which are converted into the fumarate, MS: m/e 473 (M+H+, 1Br).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phases are washed with saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. customThe brown oil is purified on silica gel with ethyl acetate/methanol (9:1)

Sources & evidence

ORD record
ord-4dff54704678443abb5e871a3498343f
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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