Hydrochloric Acid → HCID 131721073, compound

HRID 342684Notes

Reaction equation

HRID 342684 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].[C:37]1([CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])[O-].[K+].[K+].[ClH:55]>C(#N)C.CN(C=O)C.C(Cl)Cl.CCOCC>[OH2:29].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:30][CH2:31][N:46]3[CH2:47][CH2:48][CH:43]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH2:44][CH2:45]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:23])[F:22])[CH:20]=3)[C:11](=[O:29])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:30][CH2:31][N:46]3[CH2:47][CH2:48][CH:43]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH2:44][CH2:45]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:23])[F:22])[CH:20]=3)[C:11](=[O:29])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[ClH:55]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 11261695HCID 11261695, compound

Product 1

HCID 131721073HCID 131721073, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2 g of the compound obtained in step B of EXAMPLE 9, 0.67 g of 4-phenylpiperidine and 1.43 g of potassium carbonate in 6 ml of acetonitrile and 6 ml of DMF is heated at 80° C. for 4 hours. The reaction mixture is concentrated under vacuum, the residue is extracted with AcOEt, the organic phase is washed three times with water and with saturated sodium chloride solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/MeOH mixture (from 100/1; v/v to 100/3; v/v) as the eluent. The product obtained is dissolved in DCM, acidified to pH 1 by the addition of a saturated solution of gaseous HCl in ether and concentrated under vacuum to give 0.39 g of the expected product after crystallization from pentane. M.p.=126°-130° C.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. extractionthe residue is extracted with AcOEt
  3. washthe organic phase is washed three times with water
  4. dry with materialwith saturated sodium chloride solution and dried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica using a DCM/MeOH mixture (from 100/1; v/v to 100/3; v/v) as the eluent
  7. customThe product obtained
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d4cddf433ffb4e4a99a5b3bd929bfd87
Source dataset
uspto-grants-1999_01
Patent number
US05859029

Reaction notes

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