1-[(5-Hydroxy-2-pyridinyl)carbonyl]-piperidine → 2-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridine

HRID 551582Notes

Reaction equation

HRID 551582 reaction equation
[N:1]1([CH2:7][C:8]2[N:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.OC1C=[CH:18][C:19]([C:22]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=O)=NC=1>C1COCC1>[NH3:1].[N:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:18][CH2:19][CH2:22][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:12][N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 445154541-[(5-Hydroxy-2-pyridinyl)carbonyl]-piperidineHCID 445154576-Piperidin-1-ylmethyl-pyridin-3-ol

Product 2

HCID 222AmmoniaYield 4%HCID 111745632-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridineYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

6-Piperidin-1-ylmethyl-Pyridin-3-ol. To a solution of (5-hydroxy-pyridin-2-yl)-piperidin-1-yl-methanone (1.30 g, 6.31 mmol) in THF (100 mL) was added borane-dimethylsulfide complex (1.75 mL, 18.9 mmol). After 18 h the solvent was removed and the residue was diluted with MeOH (50 mL) and heated to 60° C. After 2 h the solvent was evaporated and chromatography of the residue (SiO2: 4-8% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.225 g, 17%).

Workup

  1. customAfter 18 h the solvent was removed
  2. additionthe residue was diluted with MeOH (50 mL)
  3. customAfter 2 h the solvent was evaporated

Sources & evidence

ORD record
ord-b95d4b67a1654cdd93e56e39013b7500
Source dataset
uspto-grants-2011_05
Patent number
US07947718B2

Reaction notes

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