Sodium Carbonate → 4-Benzylmorpholine-2-carbonitrile

HRID 2364670Notes

Reaction equation

HRID 2364670 reaction equation
[CH2:1]([N:8]([CH2:14][CH2:15][OH:16])[CH2:9][CH:10](Cl)[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(C)(C)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:14][CH2:15][O:16][CH:10]([C:11]#[N:12])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 23665647Potassium tert-butoxideHCID 68107675HCID 68107675, compound

Product 1

HCID 156511954-Benzylmorpholine-2-carbonitrileYield 44.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude compound 3-(benzyl(2-hydroxyethyl)amino)-2-chloro-propanenitrile 2b (8 g, 0.03 mol) was dissolved in 70 mL of tetrahydrofuran followed by the addition of potassium tert-butanolate (5.50 g, 0.05 mol) in an ice-water bath. The resulting solution was stirred for 2 hours, heated to reflux for 1 hour, added with 50 mL of saturated sodium carbonate solution, and extracted with ethyl acetate (40 mL×3). The combined organic phase was washed with saturated sodium chloride solution (50 mL×3), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 4-benzylmorpholine-2-carbonitrile 2c (2.71 g, yield: 41.0%) as a yellow oil liquid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. extractionextracted with ethyl acetate (40 mL×3)
  4. washThe combined organic phase was washed with saturated sodium chloride solution (50 mL×3)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-72a6f8895baf40e2afb4a9bd2d9d1c19
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

Loading…