1-(3-Aminopropyl)-4-methylpiperazine → HCID 68858417, compound

HRID 1986217Notes

Reaction equation

HRID 1986217 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16](Cl)[N:15]=3)[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][NH2:32])[CH2:25][CH2:24]1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([NH:32][CH2:31][CH2:30][CH2:29][N:26]4[CH2:25][CH2:24][N:23]([CH3:22])[CH2:28][CH2:27]4)[N:15]=3)[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 81531DiisopropylethylamineHCID 86625360HCID 86625360, compound

Product 1

HCID 68858417HCID 68858417, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred suspension of 2-(2,5-dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid methyl ester (440 mg, 1.30 mmol) in 1,4-dioxane (10 mL) is treated with 3-(4-methyl-piperazin-1-yl)- propylamine (610 mg, 3.90 mmol) and diisopropylethylamine (500 mg, 3.90 mmol), the resultant mixture is heated at 90° C. under nitrogen for 16 hours. After concentration and subsequent chromatographic purification on silica gel, eluting with 2 M NH3/MeOH in dichloromethane 1-10%, the title compound is isolated as a solid (310 mg, 51% yield).

Workup

  1. concentrationAfter concentration and subsequent chromatographic purification on silica gel
  2. washeluting with 2 M NH3/MeOH in dichloromethane 1-10%

Sources & evidence

ORD record
ord-7e5f7c75e5b94e57bdf3c22191963f96
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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