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

HRID 968758Notes

Reaction equation

HRID 968758 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.[CH3:20][S:21]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](O)=[O:28])(=[O:23])=[O:22].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: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][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][CH:32]=[C:24]([S:21]([CH3:20])(=[O:23])=[O:22])[CH:25]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2203803-Methanesulfonylbenzoic acidHCID 2733179PyBroPHCID 113241264-(3,4-Dichlorophenoxy)-1-piperidinepropanamine

Product 1

HCID 69522861N-{3-[4-(3,4-dichlorophenoxy)-1-piperidinyl]propyl}-3-(methylsulfonyl)benzamide hydrochlorideYield 112.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Step (b) (0.15 g) was dissolved in DMF (4 ml). 3-Methylsulphonyl-benzoic acid (0.110 g), triethylamine (0.250 ml) and PyBrop® (0.350 g) were added. After 8 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%)) and formation of the hydrochloride salt by addition of HCl dissolved in ether and evaporation of solvent gave the title compound (0.145 g).

Workup

  1. customAfter 8 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%)) and formation of the hydrochloride salt
  7. additionby addition of HCl
  8. dissolutiondissolved in ether
  9. customevaporation of solvent

Sources & evidence

ORD record
ord-acfa97f39fcc4368b2837b5b4bd2e677
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

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