Methyl iodide → HCID 19420471, compound

Temperature

95 °C

To a solution of homopiperazine (5 g, 50 mmol) in 10 mL of ethanol added a solution of methyl iodide (0.62 mL, 10 mmol) in 5 mL of ethanol in a sealed tube. It was gently stirred at 95° C. for 5 hours. The resulting white precipitate was filtered, washed with a small amount of cold ethanol, and the filtrate was concentrated in vacuo to yield 1-methyl homopiperazine hydroiodide. MS m/z M+H=115. The obtained 1-methylhomopiperazine hydroiodide is converted into free base according to the procedure describing in Example 25. Following the procedure of Example 6, but replacing 1-benzylpiperazine with 1-methyl homopiperazine, provides the desired compound. The product of Example 3 (2.1 g, 2.03 mmol), 1-methylhomopiperazine (700 mg, 6.09 mmol), and triethylamine (0.85 mL, 6.09 mmol) in 10 mL of methylene chloride are used. The reaction is carried out at 45° C. for 15 hours. Semi-pure compound is isolated from silica gel column chromatography. The obtained product (1.0 g, 0.9 mmol) is treated with 48%-HF (4 mL) in 30 mL of acetonitrile in the procedure described in Example 5. The pure title compound is isolated from silica gel column chromatography, followed by reverse phase HPLC.

1. filtrationThe resulting white precipitate was filtered
2. washwashed with a small amount of cold ethanol
3. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-d0cafc579d1f4f169158810f1a092a11

Source dataset

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05530119