Piperazine → 2-(2-Phenoxyethylamino)-3-(1-piperazinyl)pyrazine

HRID 493281Notes

Reaction equation

Cl[C:2]1[C:7]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:6][CH:5]=[CH:4][N:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.C(Cl)Cl.C(Cl)(Cl)Cl>[O:11]([CH2:10][CH2:9][NH:8][C:7]1[C:2]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:3][CH:4]=[CH:5][N:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of the product from Step 1 above (1.59 g, 6.37 mmol), piperazine (1.56 g, 18.2 mmol), and K2CO3 (0.88 g, 6.4 mmol) in acetonitrile (10 mL) was stirred at 140° C. for 12 h in a sealed tube. After cooling, the reaction mixture was diluted with CH2Cl2, filtered, and concentrated. The semisolid residue was purified by chromatography on silica gel using CHCl3/MeOH (9:1) as eluent to give a beige oil. This oil was redissolved in CHCl3, and filtered through a short (3 cm) plug of alumina covered with K2CO3. The pad was washed with several portions of CHCl3 and the resulting filtrate was concentrated to afford 1.48 g (78%) of the title product as a pale yellow oil. HRMS m/z calcd for C16H21N5O (M)+ 299.1746, found 299.1753. Anal. (C16H21N5O.1/3H2O) C, H, N.

Workup

temperatureAfter cooling
filtrationfiltered
concentrationconcentrated
customThe semisolid residue was purified by chromatography on silica gel
customto give a beige oil
filtrationfiltered through a short (3 cm) plug of alumina
washThe pad was washed with several portions of CHCl3
concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record: ord-9d7f3a1d07fa4c13a98967a049dc4a69
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534794B2

Reaction notes

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