Hydrochloric Acid → 1-(Pyridin-3-yl)piperazin-2-one

HRID 2213046Notes

Reaction equation

HRID 2213046 reaction equation
O[CH2:2][CH2:3][NH:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:7].C(P(CCCC)CCCC)CCC.Cl.C(N(CC)CC)C>O1CCCC1>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([N:8]2[CH2:2][CH2:3][NH:4][CH2:5][C:6]2=[O:7])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13831TributylphosphineHCID 218650052-[(2-Hydroxyethyl)amino]-N-3-pyridinylacetamide

Product 1

HCID 218650091-(Pyridin-3-yl)piperazin-2-oneYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Bis(1,1-dimethylethyl)diazenedicarboxylate (4.1 g, 18 mmol) in tetrahydrofuran (100 mL) was added dropwise to a stirred, cooled (0° C.) solution of 2-[(2-hydroxyethyl)amino]-N-(3-pyridinyl)acetamide (Description 142, 2.5 g, 13 mmol) and tributylphosphine (4.2 mL, 16.9 mmol) in tetrahydrofuran (300 mL) and the mixture was stirred at room temperature for 16 hours. Ethereal hydrogen chloride (1M, 10 mL) was added and the mixture was stirred at room temperature for 1 hour. Triethylamine (6 mL, 42 mmol) was added the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) (90:10:1), to give the title compound (800 mg, 35%). m/z (ES+) 178 (M+1).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customwas evaporated under reduced pressure
  3. customthe residue was purified by flash column chromatography on silica gel
  4. washeluting with CH2Cl2/MeOH/NH3(Aq.) (90:10:1)

Sources & evidence

ORD record
ord-01700779e19543c6b62083ede2d2f3fa
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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