4-Piperidinepropanol → HCID 67341654, compound

HRID 1846615Notes

Reaction equation

HRID 1846615 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[C:9](Cl)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)=[O:6].[NH:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][OH:28])[CH2:21][CH2:20]1>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[C:9]([N:19]2[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][OH:28])[CH2:21][CH2:20]2)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)=[O:6]

Participants

5

Reactant 2

HCID 814974-PiperidinepropanolHCID 86676282HCID 86676282, compound

Product 1

HCID 67341654HCID 67341654, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.200 g (0.663 mmol) of 3-chloro-N-(2,5-dichloro-pyridin-3-yl)-benzamide and 0.190 g (1.33 mmol) of 3-piperdin-4-yl-propan-1-ol in N,N-dimethylformamide (5 mL) is heated to 130° C. and stirred for 2 days. The mixture is cooled to room temperature, diluted with water, and extracted with ethyl acetate. The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 0.130 g (47%) of 3-chloro-N-[5′-chloro-4-(3-hydroxy-propyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl]-benzamide as a light brown foam.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-e992835738cb40e3ab651851914dce4b
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

Loading…