4-(6-Bromo-2-pyridinyl)-1-methyl-4-piperidinol → HCID 18771801, compound

HRID 460221Notes

Reaction equation

HRID 460221 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2(O)[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1>OS(O)(=O)=O>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 187720024-(6-Bromo-2-pyridinyl)-1-methyl-4-piperidinol

Product 1

HCID 18771801HCID 18771801, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a 150 mL flask containing 6-bromo-1′-methyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol (5 g, 18.5 mmol) was added conc. H2SO4 (50 mL). Heated to 100° C. for 18 h. Cooled and poured onto ice carefully. Neutralized with 5 N NaOH and extracted with EtOAc. Washed with brine, dried (MgSO4) and concentrated in vacuo. Diluted residue with EtOAc and filtered. Concentrated filtrate in vacuo to give 6-bromo-1′-methyl-1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl as an orange oil. MS m/z: 254.2 (M+H). Calc'd for C11H13BrN2 253.14.

Workup

  1. temperatureCooled
  2. additionpoured onto ice carefully
  3. extractionNeutralized with 5 N NaOH and extracted with EtOAc
  4. washWashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. filtrationDiluted residue with EtOAc and filtered

Sources & evidence

ORD record
ord-bb65332ad1064faf966f59dd1b7ef951
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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