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Piperazine → HCID 45379959, compound

HRID 600283
Notes
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Reaction equation

HRID 600283 reaction equation
Cl[C:2]1[C:3](=[O:19])[N:4]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH3:18])[C:5]2[CH:11]=[C:10]([Cl:12])[N:9]=[CH:8][C:6]=2[N:7]=1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C.C(OCC)(=O)C.CCCCCC>C1COCC1>[Cl:12][C:10]1[N:9]=[CH:8][C:6]2[N:7]=[C:2]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:3](=[O:19])[N:4]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH3:18])[C:5]=2[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4837PiperazineHCID 8471TriethylamineHCID 21226206Ethyl acetate hexaneHCID 453799573,7-Dichloro-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one

Product 1

HCID 45379959HCID 45379959, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of 3,7-dichloro-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one (193 mg, 0.64 mmol), piperazine (118 mg, 0.91 mmol, Aldrich) and triethylamine (0.15 mL, 1.07 mmol) in THF (3 mL) was stirred at room temperature for one hour. The reaction was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and solvent was removed at reduced pressure to give a brown oil. This was passed through a column of silica gel with 80-100% ethyl acetate/hexane to give 7-chloro-3-(piperazin-1-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one. (183 mg, 72% yield).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate, and solvent
  6. customwas removed at reduced pressure
  7. customto give a brown oil

Sources & evidence

ORD record
ord-07b5e88de17046c1b90006367b2852db
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902195B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes