Ammonium Chloride → 1-(4-Ethylpiperazin-1-yl)-3-[4-(3-hydroxy-3-methylbutyl)phenyl]isoquinoline dihydrochloride

HRID 1814564Notes

Reaction equation

HRID 1814564 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](=[O:29])[CH3:28])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH3:30][Mg]Br.CCOCC.[Cl-:38].[NH4+]>O1CCCC1>[ClH:38].[ClH:38].[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][C:27]([OH:29])([CH3:30])[CH3:28])=[CH:23][CH:24]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 225031951-(4-Ethylpiperazin-1-yl)-3-[4-(3-oxobutyl)phenyl]isoquinolineHCID 178467822HCID 178467822, compound2×

Product 1

HCID 225029971-(4-Ethylpiperazin-1-yl)-3-[4-(3-hydroxy-3-methylbutyl)phenyl]isoquinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The resulting 1-(4-ethylpiperazin-1-yl)-3-[4-(3-oxobutyl)phenyl]isoquinoline (0.50 g) was dissolved in tetrahydrofuran (50 ml), and the mixture was stirred under ice-cooling, to which was then added 3.0M methylmagnesium bromide/ether solution (860 μl). The resulting mixture was stirred for 30 min. Then, 3.0M methylmagnesium bromide/ethyl ether solution (860 μl) was additionally added thereto, and the resulting mixture was stirred for 2 hr. An aqueous solution of saturated ammonium chloride was added to the mixture and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (toluene/acetone system), to give 0.21 g of the free compound of the title compound as a colorless viscous oil.

Workup

  1. temperaturecooling, to which
  2. stirringThe resulting mixture was stirred for 30 min
  3. stirringthe resulting mixture was stirred for 2 hr
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (toluene/acetone system)

Sources & evidence

ORD record
ord-246ff9cec7c74ec99e988ec764541005
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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