Hydrochloric Acid → 1-(Pyridin-2-yl)piperazin-2-one
Reaction equation
O[CH2:2][CH2:3][NH:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:7].C(P(CCCC)CCCC)CCC.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.Cl>C1COCC1.C(OCC)C.CO.N>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:8]1[CH2:2][CH2:3][NH:4][CH2:5][C:6]1=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 40 °C
Procedure
A stirred suspension of 2-(2-hydroxyethylamino)-N-pyridin-2-yl-acetamide (0.17 g, 0.87 mmol) under an inert atmosphere in THF (3 mL) was cooled to 0–5° C. Tributyl phosphine (0.32 mL, 1.15 mmol) was added followed by a solution of di-tert-butylazodicarboxylate (0.29 g, 1.23 mmol) in THF (3 mL) dropwise over 15 min. After a further 15 min. the mixture was warmed to 40° C. and a hydrogen chloride solution in diethylether (1M, 1.8 mL) added to produce a precipitate. The mixture was cooled to 0–5° C. and the solids filtered off to give a hydroscopic product. This was dissolved in MeOH—NH3 and chromatographed on silica gel, eluting with DCM:MeOH (100:0 to 90:10), to afford the title compound (100 mg, 65%) as a colourless solid. 1H NMR (360 MHz, d6-DMSO) δ 2.85 (1H, br s), 3.01 (2H, t, J=5.5 Hz), 3.44 (2H, s), 3.82 (2H, t, J=5.5 Hz), 7.17–7.22 (1H, m), 7.75–7.86 (2H, m), 8.41–8.45 (1H, m). MS (ES+) 178 (M+1).
Workup
- temperaturewas cooled to 0–5° C
- customto produce a precipitate
- temperatureThe mixture was cooled to 0–5° C.
- filtrationthe solids filtered off
- customto give a hydroscopic product
- customchromatographed on silica gel
- washeluting with DCM:MeOH (100:0 to 90:10)
Sources & evidence
- ORD record
- ord-3088f2a6f041411a8a5eccdf0bf91863
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07144887B2
Reaction notes
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