Hydrochloric Acid → HCID 22502772, compound

HRID 1251118Notes

Reaction equation

HRID 1251118 reaction equation
C1CO[C:3]2([CH2:8][CH2:7][N:6]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[N:16]=[C:17]([N:25]5[CH2:30][CH2:29][N:28]([CH2:31][CH3:32])[CH2:27][CH2:26]5)[C:18]5[C:23]([CH:24]=4)=[CH:22][CH:21]=[CH:20][CH:19]=5)=[CH:11][CH:10]=3)[CH2:5][CH2:4]2)[O:2]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[ClH:50]>CO>[ClH:50].[ClH:50].[ClH:50].[CH2:31]([N:28]1[CH2:29][CH2:30][N:25]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:24]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([N:6]4[CH2:5][CH2:4][CH:3]([OH:2])[CH2:8][CH2:7]4)=[CH:10][CH:11]=3)[N:16]=2)[CH2:26][CH2:27]1)[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 22503240HCID 22503240, compound

Product 1

HCID 22502772HCID 22502772, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[4-(4,4-Ethylenedioxypiperidin-1-yl)phenyl]-1-(4-ethylpiperazin-1-yl)isoquinoline (290 mg) obtained in Example 96 was treated with camphorsulfonic acid and methanol. Then, a 2N aqueous solution of hydrochloric acid (50 ml) was added thereto, and the mixture was reacted for 1 hr. The reaction solution was basified and extracted with ethyl acetate. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, the resulting residue was dissolved in methanol (20 ml), and then it was reacted with sodium borohydride (54 mg). The reaction solution was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 119 mg of the free compound of the title compound as a white solid.

Workup

  1. customthe mixture was reacted for 1 hr
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. dissolutionthe resulting residue was dissolved in methanol (20 ml)
  7. customit was reacted with sodium borohydride (54 mg)
  8. customThe reaction solution was evaporated
  9. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-a3db32b2974146088ccaa9aa673f57b4
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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