Hydrazine hydrate (1:1) → HCID 18771814, compound

HRID 460170Notes

Reaction equation

HRID 460170 reaction equation
C1(=O)[N:5]([C:6]2[C:11]([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:10][CH:9]=[CH:8][N:7]=2)C(=O)C2=CC=CC=C12.O.NN>CCO>[NH2:5][C:6]1[C:11]([CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 187716212-[3-(1-Piperidinylmethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 18771814HCID 18771814, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(Phthalimidyl)-3-(1-piperidinylmethyl)-pyridine (196 mg, 0.609 mmol) was dissolved in EtOH (95%, 2 mL) at 23° C., and treated with hydrazine monohydrate (0.0320 mL, 0.670 mmol) in a dropwise fashion. The resulting mixture was warmed to reflux and stirred for 3 h at reflux. The solution was treated with additional hydrazine monohydrate (0.150 mL, 3.050 mmol), and reflux continued. After 14 h at reflux, the mixture was cooled to RT, and concentrated using a rotary evaporator to a white paste. The resulting white paste was dissolved in CHCl3: IpOH (3:1, 75 mL), and washed with saturated NaHCO3 (3×50 mL), and H2O (1×50 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to provide the title compound as a white solid. MS m/z: 192 (M+H).

Workup

  1. temperatureThe resulting mixture was warmed
  2. temperatureto reflux
  3. temperatureat reflux
  4. temperaturereflux
  5. temperatureAfter 14 h at reflux
  6. concentrationconcentrated
  7. customa rotary evaporator to a white paste
  8. dissolutionThe resulting white paste was dissolved in CHCl3
  9. washIpOH (3:1, 75 mL), and washed with saturated NaHCO3 (3×50 mL), and H2O (1×50 mL)
  10. dry with materialThe organic layer was dried over MgSO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25d8e01d0aaa44c59b971f14448c0d0f
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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