Trifluoroacetic acid → HCID 23513749, compound

HRID 1281989Notes

Reaction equation

HRID 1281989 reaction equation
[CH2:1]([N:3]([CH2:37][CH3:38])[C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH:23]2[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]2)([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)O)=[CH:7][CH:6]=1)[CH3:2].FC(F)(F)C(O)=O>CCOC(C)=O>[CH2:37]([N:3]([CH2:1][CH3:2])[C:4](=[O:36])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)=[C:23]2[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]2)=[CH:9][CH:10]=1)[CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23435924HCID 23435924, compound

Product 1

HCID 23513749HCID 23513749, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound of Example 19 (45 mg), trifluoroacetic acid (1.0 mL) and trifluoromethanesulforic acid (1 mL) was refluxed for 8 hrs., and then condensed. The residue was dissolved in AcOEt (50 ml). The resulting solution was washed with 1 N NaOH solution, aqueous NH4Cl solution and brine, dried over Na2SO4. Removal of solvents gave a crude product, which was purified by silica gel column eluting with NH4OH (1N)-MeOH—CH2Cl2 (2.5:17.5:80) to provide N,N-diethyl-4-(8-quinolinyl-piperidin-4-ylidene-methyl)-benzamide (29 mg, 84%):

Workup

  1. temperaturewas refluxed for 8 hrs
  2. custom, and then condensed
  3. washThe resulting solution was washed with 1 N NaOH solution, aqueous NH4Cl solution and brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of solvents
  6. customgave a crude product, which
  7. customwas purified by silica gel column
  8. washeluting with NH4OH (1N)-MeOH—CH2Cl2 (2.5:17.5:80)

Sources & evidence

ORD record
ord-e24425017772460787eb5648da7994b4
Source dataset
uspto-grants-2002_09
Patent number
US06455545B2

Reaction notes

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