1-(Piperidin-4-yl)ethan-1-ol → HCID 67340994, compound

HRID 1846619Notes

Reaction equation

HRID 1846619 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]([OH:9])[CH3:8])[CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:25]=[CH:26][CH:27]=1)[C:14]([NH:16][C:17]1[C:18](Cl)=[N:19][CH:20]=[C:21]([Cl:23])[CH:22]=1)=[O:15]>C(#N)C>[Cl:10][C:11]1[CH:12]=[C:13]([CH:25]=[CH:26][CH:27]=1)[C:14]([NH:16][C:17]1[C:18]([N:1]2[CH2:6][CH2:5][CH:4]([CH:7]([OH:9])[CH3:8])[CH2:3][CH2:2]2)=[N:19][CH:20]=[C:21]([Cl:23])[CH:22]=1)=[O:15]

Participants

4

Reactant 2

HCID 3383211-(Piperidin-4-yl)ethan-1-olHCID 86676282HCID 86676282, compound

Product 1

HCID 67340994HCID 67340994, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.200 g (1.55 mmol) of 1-piperidin-4-yl-ethanol and 0.200 g (0.663 mmol) of 3-chloro-N-(2,5-dichloro-pyridin-3-yl)-benzamide in acetonitrile (10 mL) is heated at 175 C in a microwave reactor for 14 hours. The mixture is cooled to room temperature and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to give 0.170 g (65.0%) of 3-chloro-N-[5′-chloro-4-(1-hydroxy-ethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl]-benzamide as a yellow oil.

Workup

  1. temperatureis heated at 175 C in a microwave reactor for 14 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-ea4d7f7ac0354d6581df8ee017e4dead
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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