Triethylamine → 1-(Pyridin-4-yl)piperidin-4-ol

HRID 395859

Reaction equation

HRID 395859 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>CCO.O>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 142684-BromopyridineHCID 79341Piperidin-4-ol

Product 1

HCID 234476191-(Pyridin-4-yl)piperidin-4-olYield 53.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-hydroxypiperidine (7.80 g, 77 mmol), 4-bromopyridine (15.0 g, 77 mmol), and triethylamine (32 mL, 231 mmol) in 90 mL of EtOH and 30 mL of H2O was heated at 150° C. in a sealed tube for 4 days. The mixture was concentrated and the residue partitioned between CH2Cl2 and H2O. The organic layer was washed with 1 N NaOH (2×), diluted with EtOAc and the resulting solid collected by filtration affording 7.30 g (53%) of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between CH2Cl2 and H2O
  3. washThe organic layer was washed with 1 N NaOH (2×)
  4. additiondiluted with EtOAc
  5. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-35703a1d153c43d78676c3989b2fdae7
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Linked notes

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