Phenethyl bromide → HCID 11680181, compound

HRID 1586439Notes

Reaction equation

HRID 1586439 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.[NH2-].[Na+].Br[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[C:15]1([CH2:14][CH2:13][CH:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:8]#[N:9])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 24533Sodium amideHCID 809233-Pyridineacetonitrile

Product 1

HCID 11680181HCID 11680181, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-35 °C

Procedure

A solution of 3-pyridylacetonitrile (23 g) in tetrahydrofuran (75 ml) was added dropwise to a stirred suspension of sodium amide (8 g) in tetrahydrofuran (175 ml) under a nitrogen atmosphere at 0° C. After complete addition of the solution, the resultant mixture was stirred at 0-10° C. for 1 hour, then cooled to -35° C. and a solution of 2-(bromoethyl)benzene (36 g) in tetrahydrofuran (100 ml) was added dropwise over 30 minutes. The resultant new mixture was stirred between -35° C. to ambient temperature overnight, then quenched with water and neutralized with 10% hydrochloric acid. After the removal of of tetrahydrofuran, the residue was dissolved in methylene chloride and washed with saturated sodium bicarbonate solution. The organic extract was then dried over magnesium sulfate, filtered and evaporated to give an oil. The oil was then distilled to provide 30 g of α-(2-phenylethyl)-3-pyridineacetonitrile, b.p.=170-173° C./0.5 mmHg.

Workup

  1. additionAfter complete addition of the solution
  2. customquenched with water and neutralized with 10% hydrochloric acid
  3. customAfter the removal of of tetrahydrofuran
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washwashed with saturated sodium bicarbonate solution
  6. extractionThe organic extract
  7. dry with materialwas then dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto give an oil
  11. distillationThe oil was then distilled

Sources & evidence

ORD record
ord-b2c78f12533947d5a59404cbf7a9dd53
Source dataset
uspto-grants-1999_08
Patent number
US05945436

Reaction notes

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