HCID 18771591, compound → HCID 18771901, compound

HRID 460195Notes

Reaction equation

HRID 460195 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=O)[CH:5]=[CH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:10]1([CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 18771591HCID 18771591, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18771901HCID 18771901, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (2-amino-pyridin-4-yl)-piperidin-1-yl-methanone (100 mg, 0.487 mmol) in dry THF (10 mL) at 0° C. was added LAH (1.5 mL, 1.46 mmol) dropwise. The mixture was heated to reflux for 20 h. The resulting mixture was cooled to 0° C. and quenched with H2O (1.5 mL) dropwise followed by 10% NaOH (1.5 mL). Solvent was removed and the residue was partitioned between H2O and CHCl3. The organic layer was washed with H2O, brine, dried over MgSO4. Concentration in vacuo gave a light brown liquid. MS m/z: 192.2 (M+H). Calc'd. for C11H17N3-191.14.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 20 h
  3. customquenched with H2O (1.5 mL)
  4. customSolvent was removed
  5. customthe residue was partitioned between H2O and CHCl3
  6. washThe organic layer was washed with H2O, brine
  7. dry with materialdried over MgSO4
  8. concentrationConcentration in vacuo
  9. customgave a light brown liquid

Sources & evidence

ORD record
ord-c7953c898401490dbbd3ba8004a943ec
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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