1-(3-Aminopropyl)-4-methylpiperazine → [4-(Benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine tri-hydrochloride

HRID 1986220

Reaction equation

HRID 1986220 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.[S:12]1[C:16]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[N:18]=2)=[CH:15][C:14]2[CH:24]=[CH:25][CH:26]=[CH:27][C:13]1=2>O1CCOCC1>[ClH:23].[ClH:23].[ClH:23].[S:12]1[C:16]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:1][CH2:2][CH2:3][CH2:4][N:5]3[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH2:10]3)[N:18]=2)=[CH:15][C:14]2[CH:24]=[CH:25][CH:26]=[CH:27][C:13]1=2

Participants

4

Reactant 2

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 147450254-(1-Benzothiophen-2-yl)-2-chloropyrimidine

Product 1

HCID 68855962[4-(Benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine tri-hydrochlorideYield 213.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-(3-Aminopropyl)-4-methylpiperazine (3.02 g, 19.2 mmol) is added to a stirred suspension of 4-(benzo[b]thiophen-2-yl)-2-chloro-pyrimidine (2.06 g, 8.34 mmol) in anhydrous 1,4-dioxane (25 mL) at ambient temperature under nitrogen. The resultant mixture is heated in an oil bath at 95° C. for 28 hours. At ambient temperature the mixture is concentrated and subject to chromatographic purification on silica gel, eluting with 2 M NH3/CH3OH in dichloromethane 0-6%, to give the free base of the title compound as a white solid (2.83 g, 92% yield).

Workup

  1. concentrationAt ambient temperature the mixture is concentrated
  2. customsubject to chromatographic purification on silica gel
  3. washeluting with 2 M NH3/CH3OH in dichloromethane 0-6%

Sources & evidence

ORD record
ord-c84c9e76168d4ed0b7b9f3c27344efb4
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Linked notes

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