Water → N-{3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl}-5-pyridin-2-ylthiophene-2-sulfonamide

HRID 1394044Notes

Reaction equation

HRID 1394044 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][NH2:15])[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[S:36][C:35]([S:37](Cl)(=[O:39])=[O:38])=[CH:34][CH:33]=1.O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][NH:15][S:37]([C:35]2[S:36][C:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=3)=[CH:33][CH:34]=2)(=[O:38])=[O:39])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chlorideHCID 113241264-(3,4-Dichlorophenoxy)-1-piperidinepropanamine

Product 1

HCID 9849759N-{3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl}-5-pyridin-2-ylthiophene-2-sulfonamideYield 38.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The product of Example 2, Step (b) (0.2 g) was dissolved in acetone (4 ml). Potassium carbonate [0.130 g dissolved in H2O (1 ml)] was then added, followed by 5-pyridin-2-yl-thiophene-2-sulfonyl chloride (0.171 g) and the reaction left to stir for 10 mins. Water was then added and the product extracted with ethyl acetate. The combined organic extracts dried, filtered and concentrated. Purification by reverse phase HPLC {with a gradient eluent system [30% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)]} gave the title compound as a solid (0.135 g).

Workup

  1. waitthe reaction left
  2. extractionthe product extracted with ethyl acetate
  3. customThe combined organic extracts dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by reverse phase HPLC {with a gradient eluent system [30% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)]}

Sources & evidence

ORD record
ord-c7453c77fd9a4a578f13d05c740f16a4
Source dataset
uspto-grants-2008_03
Patent number
US07348341B2

Reaction notes

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