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Water → 1-(2-Benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazin-4-yl)-7-methoxyisoquinoline

HRID 1714805
Notes
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Reaction equation

HRID 1714805 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][NH:15][CH2:14][CH2:13][N:12]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=2)[CH:28]=[CH:27][N:26]=1.C(N(CC)CC)C.O>C(O)CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][N:15]([C:25]4[C:34]5[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=5)[CH:28]=[CH:27][N:26]=4)[CH2:14][CH2:13][N:12]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:9][C:4]=2[O:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 222501811-Chloro-7-methoxyisoquinolineHCID 231556182-Benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazine

Product 1

HCID 231558011-(2-Benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazin-4-yl)-7-methoxyisoquinolineYield 44%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 320 mg of 2-benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazine as synthesized in the above step, 200 mg of 1-chloro-7-methoxyisoquinoline and 100 mg of triethylamine was stirred in 2 ml of ethylene glycol at 150° C. for 18 hours. After addition of water, the solution was 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 (ethyl acetate:n-hexane=1:1) to provide 210 mg (44%) of 1-(2-benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazin-4-yl)-7-methoxyisoquinoline.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified on silica gel column chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-89884b65e752497cbe03964188c7a8bd
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07799775B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes