Triethylamine → [4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(2-methanesulfonyl-phenyl)-methanone

HRID 1293528Notes

Reaction equation

HRID 1293528 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][S:8]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O)(=[O:10])=[O:9].[Cl:20][C:21]1[CH:22]=[C:23]([CH:37]=[CH:38][C:39]=1[Cl:40])[O:24][CH:25]1[CH2:30][CH2:29][N:28]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:27][CH2:26]1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:37]=[CH:38][C:39]=1[Cl:40])[O:24][CH:25]1[CH2:26][CH2:27][N:28]([CH:31]2[CH2:32][CH2:33][N:34]([C:13]([C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:8]([CH3:7])(=[O:9])=[O:10])=[O:15])[CH2:35][CH2:36]2)[CH2:29][CH2:30]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2843422-Methanesulfonylbenzoic acidHCID 223974344-(3,4-Dichloro-phenoxy)-[1,4']bipiperidine

Product 1

HCID 22397458[4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(2-methanesulfonyl-phenyl)-methanoneYield 76.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent4×

Procedure

Oxalyl chloride (55 ml, 0.63 mol) was added dropwise over 10 minutes to a stirred suspension of 2-methanesulfonyl-benzoic acid (7.1 g, 0.036) in DCM (550 ml) containing DMF (0.5 ml). The solution was then stirred for 2 hours at room temperature. The solution was then evaporated to give a solid that was redissolved in dichloromethane and again evaporated to give a yellow solid. The solid acid chloride was dissolved in DCM (275 ml) and was added over 10 minutes to a stirred solution of the product of Step 3 (11.0 g, 0.033 mol) and triethylamine (15.4 ml, 0.11 mol) in dichloromethane (125 ml). The resultant solution was stirred at room temperature for 16 hours. The solution was then washed with water (500 ml), 1M aq NaOH (500 ml) and water (2×500 ml). The organic phase was dried (MgSO4), filtered and the solvent removed to give a pale yellow foam. The foam was triturated with diethyl ether to give the title compound (12.96 g, 76%).

Workup

  1. customThe solution was then evaporated
  2. customto give a solid
  3. customagain evaporated
  4. customto give a yellow solid
  5. washThe solution was then washed with water (500 ml), 1M aq NaOH (500 ml) and water (2×500 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto give a pale yellow foam
  10. customThe foam was triturated with diethyl ether

Sources & evidence

ORD record
ord-d0b63002d76846dfb07efbe82f2758b2
Source dataset
uspto-grants-2007_07
Patent number
US07238811B2

Reaction notes

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