Triethylamine → N-{2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}-3-(methylsulfonyl)benzamide hydrochloride

HRID 968760Notes

Reaction equation

HRID 968760 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH2:14])[CH2:8][CH2:7]1.[CH3:19][S:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](O)=[O:27])(=[O:22])=[O:21].C(N(CC)CC)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][NH:14][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([S:20]([CH3:19])(=[O:22])=[O:21])[CH:24]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2203803-Methanesulfonylbenzoic acidHCID 2733179PyBroPHCID 113582094-(3,4-Dichlorophenoxy)-1-piperidineethanamine

Product 1

HCID 69522044N-{2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}-3-(methylsulfonyl)benzamide hydrochlorideYield 47.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Step b (0.200 g) was dissolved in DMF (5 ml). 3-Methylsulphonyl-benzoic acid (0.132 g), triethylamine (0.250 ml) and PyBrop® (0.420 g) were added. After 24 hours at room temperature the solvents were evaporated and the residue redissolved in ethyl acetate. The organics were washed with H2O, dried with MgSO4 and concentrated. Purification by reverse phase HPLC (with a gradient eluent system (25% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)) (any excess NH4OAc was removed by dissolving the compound in ethyl acetate and washing with aqueous saturated NaHCO3 followed by drying of the organics with MgSO4 and evaporation of solvent) and formation of the hydrochloride salt by addition of HCl dissolved in ether and evaporation of solvent gave the title compound (0.084 g).

Workup

  1. customAfter 24 hours at room temperature the solvents were evaporated
  2. dissolutionthe residue redissolved in ethyl acetate
  3. washThe organics were washed with H2O
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customPurification by reverse phase HPLC (with a gradient eluent system (25% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)) (any excess NH4OAc
  7. customwas removed
  8. dissolutionby dissolving the compound in ethyl acetate
  9. washwashing with aqueous saturated NaHCO3
  10. customby drying of the
  11. customorganics with MgSO4 and evaporation of solvent) and formation of the hydrochloride salt
  12. additionby addition of HCl
  13. dissolutiondissolved in ether
  14. customevaporation of solvent

Sources & evidence

ORD record
ord-923b376c0be44856a46b36ddc389e230
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

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