Chloroacetonitrile → 2-(4-hydroxypiperidin-1-yl)acetonitrile

HRID 1359848Notes

Reaction equation

HRID 1359848 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl[CH2:9][C:10]#[N:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:9][C:10]#[N:11])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 178418642HCID 178418642, compound

Product 1

HCID 111054492-(4-hydroxypiperidin-1-yl)acetonitrileYield 99.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-hydroxypyridine (4.04 g, 40 mmol), chloroacetonitrile (2.78 mL, 44 mmol) and potassium carbonate (22 g, 160 mmol) in acetonitrile (50 mL) was stirred at rt for overnight. The insolubles were filtered off, the filtrate was concentrated to give 5.6 g of (4-hydroxy-piperidin-1-yl)-acetonitrile.

Workup

  1. filtrationThe insolubles were filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9b2ecec2ff064a87b51db3bf718a57b7
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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