Hydrochloric Acid → HCID 9853069, compound

HRID 342683Notes

Reaction equation

HRID 342683 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:30][CH2:31]OS(C)(=O)=O)[CH2:13][N:12]([CH2:14][C:15]3[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]=3)[C:11](=[O:29])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:37][C:38]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.C(OCC)(=O)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:30][CH2:31][N:41]3[CH2:42][CH2:43][C:38]([OH:37])([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH2:39][CH2:40]3)[CH2:13][N:12]([CH2:14][C:15]3[CH:16]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:18]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:20]=3)[C:11](=[O:29])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 963874-Phenylpiperidin-4-olHCID 11261695HCID 11261695, compound

Product 1

HCID 9853069HCID 9853069, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture containing 1 g of 4-(3,4-dichlorophenyl)-1-[3,5-bis(trifluoromethyl)benzyl]-4-[2-(mesyloxy)ethyl]pyrrolidin-2-one obtained in Example 9, step B, 0.875 g of 4-hydroxy-4-phenylpiperidine and 0.483 g of potassium carbonate in 2 ml of DMF is prepared and heated at 80° C. for 3 hours. It is allowed to cool and ice, water and ethyl acetate are then added. Extraction is carried out with AcOEt and the extract is washed with water and then with sodium chloride solution. The pure product is obtained by chromatography on silica using a DCM/MeOH mixture (100/3; v/v) as the eluent. The hydrochloride is then prepared by reaction with hydrochloric acid in DCM. The expected product crystallizes from a pentane/ether mixture. m=0.555 g. M.p.=136°-138° C.

Workup

  1. customis prepared
  2. temperatureto cool
  3. extractionExtraction
  4. washthe extract is washed with water
  5. customThe pure product is obtained by chromatography on silica using a DCM/MeOH mixture (100/3; v/v) as the eluent
  6. customThe expected product crystallizes from a pentane/ether mixture

Sources & evidence

ORD record
ord-595af8cf60674ed0b4714d60974e767e
Source dataset
uspto-grants-1999_01
Patent number
US05859029

Reaction notes

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