1-(3-Aminopropyl)-4-methylpiperazine → HCID 68857906, compound

HRID 1986197Notes

Reaction equation

HRID 1986197 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[C:14]([C:16]3[C:21]([CH3:22])=[CH:20][N:19]=[C:18](Cl)[N:17]=3)[S:13][C:12]=2[CH:24]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:26][CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]1>O1CCOCC1>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[C:14]([C:16]3[C:21]([CH3:22])=[CH:20][N:19]=[C:18]([NH:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:31][CH2:32][N:33]([CH3:36])[CH2:34][CH2:35]4)[N:17]=3)[S:13][C:12]=2[CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 86625350HCID 86625350, compound

Product 1

HCID 68857906HCID 68857906, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of [2-(2-chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophen-6-yl]-carbamic acid tert-butyl ester (0.32 g, 0.85 mmol) and 1-(3-aminopropyl)-4-methylpiperazine (0.41 g, 2.6 mmol) in 1,4-dioxane (15 mL) is refluxed for 48 hours. Solvent is removed and the residue is chromatographed on silica gel, eluting with 2.0 M NH3/MeOH in dichloromethane 0-10%, to obtain the title compound as a yellow solid (0.33 g, 78% yield). ES+(m/z) 497 [M+H].

Workup

  1. temperatureis refluxed for 48 hours
  2. customSolvent is removed
  3. customthe residue is chromatographed on silica gel
  4. washeluting with 2.0 M NH3/MeOH in dichloromethane 0-10%

Sources & evidence

ORD record
ord-44f641971d424537941c58a264e9d61f
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

Loading…