Piperidin-4-ol → 2-(4-Hydroxypiperidin-1-yl)-5-nitrobenzonitrile

HRID 1744497Notes

Reaction equation

HRID 1744497 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([N:17]2[CH2:18][CH2:19][CH:14]([OH:13])[CH2:15][CH2:16]2)=[C:3]([CH:6]=1)[C:4]#[N:5])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 172213732-(4-Hydroxypiperidin-1-yl)-5-nitrobenzonitrileYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-chloro-5-nitrobenzonitrile (36 g) and 4-hydroxypiperidine (50 g) were added to ethanol (300 ml), and the mixture was stirred at a refluxing temperature for 1 h. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from hydrous ethanol to give 5-nitro-2-(4-hydroxypiperidin-1-yl)benzonitrile (37.4 g), melting point: 114–115° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionDiisopropyl ether was added to the residue
  3. customcrystallization
  4. customThe crystals were recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-ce0c44999786402aae8feda816941823
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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