Water → 2-Phenylpiperazine

HRID 1640332Notes

Reaction equation

HRID 1640332 reaction equation
O=[C:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:6][CH2:5][CH2:4][NH:3]1.O.[OH-].[Na+]>C1COCC1>[C:8]1([CH:7]2[CH2:2][NH:3][CH2:4][CH2:5][NH:6]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 2506813-Phenylpiperazin-2-one

Product 1

HCID 2506732-PhenylpiperazineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Oxo-3-phenyl-piperazine (1.76 g, 10 mmol), in 30 mL of anhydrous THF was added dropwise to a 20 mL (20 mmol) of 1M solution of LiAH4 in THF, and the mixture was stirred at room temperature for 24 h. After workup (water, 20% NaOH addition to destroy excess LiAH4), the mixture was filtered and the filter cake was reextracted with ethyl acetate. The combined organic filtrate and exam were dried over MgSO4, filtered and evaporated to give an slightly yellow solid that was purified by silica gel column chromatography (CHCl3:MeOH:NH4OH/9:1:0.1). The reduced product was isolated as a colorless solid (960 mg, 6 mmol, 60%). 1H NMR (CDCl3): δ 2.69 (1H, t, J=11.3), 2.85-3.10 (7H, m), 3.76 (1H, br d, J=8.9), 7.21-7.38 (5H, m). mp (free base): 79°-81° C.

Workup

  1. filtrationthe mixture was filtered
  2. dry with materialThe combined organic filtrate and exam were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give an slightly yellow solid
  6. customthat was purified by silica gel column chromatography (CHCl3:MeOH:NH4OH/9:1:0.1)

Sources & evidence

ORD record
ord-7328f3f295ac46008bfd5b07553e9592
Source dataset
uspto-grants-2012_02
Patent number
US08114379B2

Reaction notes

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