1-Methylpiperazine → HCID 68747598, compound

HRID 1396625Notes

Reaction equation

HRID 1396625 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:12])[CH:5]=[C:4]([C@@H:13]([NH:15]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[CH3:14])[N:3]=1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>O1CCOCC1>[Cl:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([N:37]1[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]1)=[N:3][C:4]([C@@H:13]([NH2:15])[CH3:14])=[CH:5]2

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 86665027(S)-(9H-fluoren-9-yl)methyl 1-(1,8-dichloroisoquinolin-3-yl)ethylcarbamate

Product 1

HCID 68747598HCID 68747598, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-(9H-fluoren-9-yl)methyl 1-(1,8-dichloroisoquinolin-3-yl)ethylcarbamate 69 (250 mg, 0.539 mmol, 1.0 eq) and 1-methylpiperazine (108 mg, 1.079 mmol, 2.0 eq) in 1,4-dioxane (5 mL) was stirred at reflux overnight. The reaction mixture was allowed to cool to RT and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (3.3% MeOH-DCM) to afford the product (S)-1-(8-chloro-1-(4-methylpiperazin-1-yl) isoquinolin-3-yl)ethanamine 95.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (3.3% MeOH-DCM)

Sources & evidence

ORD record
ord-2b4b6abd2874469db9be0781bf7f11a3
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

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