Sodium Carbonate → 1-[2-Bis(4-fluorophenyl)methoxyethyl]-4-piperidinecarbonitrile

HRID 487138

Reaction equation

HRID 487138 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11]Cl)=[CH:4][CH:3]=1.[C:20]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)#[N:21].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.[I-].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11][N:25]2[CH2:26][CH2:27][CH:22]([C:20]#[N:21])[CH2:23][CH2:24]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1382234-CyanopiperidineHCID 107793021-[Bis(4-fluorophenyl)methoxy]-2-chloroethane

Product 1

HCID 104509191-[2-Bis(4-fluorophenyl)methoxyethyl]-4-piperidinecarbonitrileYield 88%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

2.13 g of 1-bis(4-fluorophenyl)methoxy-2-chloroethane and 0.95 g of 4-cyanopiperidine were dissolved in 15 ml of dimethylformamide. After this, 4.00 g of anhydrous sodium carbonate and 0.08 g of sodium iodide were added to the resulting solution, and the mixture was stirred for 4 hours at 130° C. At the end of this time, the mixture was poured into ice water and extracted with ethyl acetate. The oily extract obtained was purified by silica gel chromatography. Elution with a 2:1 by volume mixture of ethyl acetate and hexane afforded 2.36 g (yield 88%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe oily extract
  3. customobtained
  4. customwas purified by silica gel chromatography
  5. washElution with a 2:1
  6. additionby volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-32fbc49995aa403aacd8c5ca99884d52
Source dataset
uspto-grants-1994_03
Patent number
US05294623

Linked notes

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