p-Bromobenzenesulfonyl chloride → HCID 18434163, compound

HRID 2306502Notes

Reaction equation

HRID 2306502 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 Hünig 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-f068c9db1448498abb60a22c585c3402
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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