4-Piperidineethanol → HCID 68303884, compound

HRID 1846613Notes

Reaction equation

HRID 1846613 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][OH:27])[CH2:21][CH2:20]1>C(#N)C>[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][OH:27])[CH2:21][CH2:20]2)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)=[O:6]

Participants

4

Reactant 2

HCID 739534-PiperidineethanolHCID 86676282HCID 86676282, compound

Product 1

HCID 68303884HCID 68303884, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1.06 g (5.00 mmol) of 3-chloro-N-(2,5-dichloro-pyridin-3-yl)-benzamide and 0.646 g (5.00 mmol) of 4-piperidine ethanol in acetonitrile (25 mL) is heated in a microwave reactor at 180° C. for 4 hours. Upon standing at room temperature a solid precipitates from solution. The solid is collected by filtration, washed with cold acetonitrile, and dried on the filter pad to provide 1.97 g (76%) of 3-chloro-N-[5′-chloro-4-(2-hydroxy-ethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl]-benzamide as a clear solid.

Workup

  1. customUpon standing at room temperature
  2. customprecipitates from solution
  3. filtrationThe solid is collected by filtration
  4. washwashed with cold acetonitrile
  5. customdried on the filter pad

Sources & evidence

ORD record
ord-e67c5fb5e17b429e8f332e199156cba2
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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