Potassium Cyanide → 2-(Cyanomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone

HRID 1252626Notes

Reaction equation

HRID 1252626 reaction equation
Cl[CH2:2][C:3]1[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.[C-:25]#[N:26].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[C:25]([CH2:2][C:3]1[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1)#[N:26]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 141824862-(chloromethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone

Product 1

HCID 141825142-(Cyanomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinoneYield 27.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2.0 g (6 mmol) of 2-(chloromethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone in 20 ml of acetonitrile was added 3.9 g (60 mmol) of potassium cyanide and 0.1 g of 18-crown-6; the mixture was heated to reflux for 2.5 hours. The salts were filtered off by suction, and the filtrate was evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel using ethyl acetate/methanol (8:2) as eluent; yielding 0.55 g of the title compound, melting point 175°-180° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. filtrationThe salts were filtered off by suction
  4. customthe filtrate was evaporated in vacuo
  5. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-83bc6622fe9e4cbeb8097ca3f189f163
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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