Hydrochloric Acid → HCID 86751146, compound

HRID 2257062Notes

Reaction equation

HRID 2257062 reaction equation
S(O[CH2:6][CH2:7][C:8]1([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=2)[CH2:13][N:12]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[C:11](=[O:29])[CH2:10][CH2:9]1)(C)(=O)=O.C([O-])([O-])=O.[K+].[K+].[C:44]1([CH:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.Cl>C(#N)C.CCOCC.CN(C=O)C>[ClH:36].[F:23][C:21]([F:24])([F:22])[C:19]1[CH:20]=[C:15]([CH:16]=[C:17]([C:25]([F:27])([F:28])[F:26])[CH:18]=1)[CH2:14][N:12]1[CH2:13][C:8]([CH2:7][CH2:6][N:53]2[CH2:54][CH2:55][CH:50]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:51][CH2:52]2)([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=2)[CH2:9][CH2:10][C:11]1=[O:29]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 54160351HCID 54160351, compound

Product 1

HCID 86751146HCID 86751146, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

2.79 g of 5-(2-mesyloxyethyl)-5-(3,4-dichlorophenyl)-1-[3,5-bis(trifluoromethyl)benzyl]piperid-2-one prepared in Example 1, step B, 1.95 g of K2CO3 and 0.91 g of 4-phenylpiperidine are mixed in 6 ml of acetonitrile and 6 ml of DMF and the mixture is heated at 80° C. for 4 hours. After evaporation of the solvents, the residue is extracted with ethyl acetate and the extract is washed with water and then with saturated NaCl solution. It is dried over MgSO4 and concentrated and the residue is then chromatographed on silica using DCM/MeOH (100/1; v/v) as the eluent. A sample of the product obtained is taken up with a solution of hydrochloric acid in ether and the solvent is evaporated off to give 0.365 g of the expected product, which crystallizes from a pentane/ether mixture. M.p.=170° C.

Workup

  1. customAfter evaporation of the solvents
  2. extractionthe residue is extracted with ethyl acetate
  3. washthe extract is washed with water
  4. dry with materialIt is dried over MgSO4
  5. concentrationconcentrated
  6. customthe residue is then chromatographed on silica
  7. customA sample of the product obtained
  8. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-42465e038dfd4dae82828ecc9864b495
Source dataset
uspto-grants-1997_08
Patent number
US05656639

Reaction notes

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