Sodium Bicarbonate → 1-(3-Benzo[1,3]dioxol-5-ylmethylpiperazin-1-yl)-7-methoxyisoquinoline

HRID 1714806Notes

Reaction equation

HRID 1714806 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][N:15]([C:17]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=5)[CH:20]=[CH:19][N:18]=4)[CH2:14][CH2:13][N:12]3C(OC(C)(C)C)=O)=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])O.[Na+]>Cl.O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[NH:12][CH2:13][CH2:14][N:15]([C:17]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=5)[CH:20]=[CH:19][N:18]=4)[CH2:16]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 231558011-(2-Benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazin-4-yl)-7-methoxyisoquinoline

Product 1

HCID 231557261-(3-Benzo[1,3]dioxol-5-ylmethylpiperazin-1-yl)-7-methoxyisoquinolineYield 58.2%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

In 10 ml of 4N hydrochloric acid-dioxane solution, 150 mg of 1-(2-benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazin-4-yl)-7-methoxyisoquinoline as synthesized in the above step was added and stirred for 18 hours. The solution was neutralized with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (methanol:chloroform=1:9) to provide 69 mg (58%) of 1-(3-benzo[1,3]dioxol-5-ylmethylpiperazin-1-yl)-7-methoxyisoquinoline.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified on silica gel column chromatography (methanol:chloroform=1:9)

Sources & evidence

ORD record
ord-fc517de01535461d928992a7e2a5de0e
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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