Ethanol → Ethyl 4-benzylmorpholine-2-carboxylate

HRID 30315Notes

Reaction equation

HRID 30315 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]#N)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:17].[CH2:21]([OH:23])[CH3:22]>>[CH2:21]([O:23][C:14]([CH:10]1[O:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)=[O:17])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 156511954-Benzylmorpholine-2-carbonitrile

Product 1

HCID 15651196Ethyl 4-benzylmorpholine-2-carboxylate

Procedure

A stirred solution of 4-benzyl-morpholine-2-carbonitrile (113.0 g, 0.56 mol) in ethanol (1030 mL) is treated with concentrated sulphuric acid (165 mL) added in portions. (exothermic, internal temperature rises from ambient to 65° C.). The mixture is then warmed under reflux for 66 hrs. The solution is cooled and then concentrated in vacuo to half volume, basified with aqueous potassium carbonate (beware frothing) and the product extracted into diethyl ether. The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness in vacuo to yield an oil. This material is evacuated further under high vacuum. Yield=121.3 g (87%).

Workup

  1. additionadded in portions
  2. custom(exothermic, internal temperature rises from ambient to 65° C.)
  3. temperatureThe mixture is then warmed
  4. temperatureunder reflux for 66 hrs
  5. temperatureThe solution is cooled
  6. concentrationconcentrated in vacuo to half volume
  7. extractionthe product extracted into diethyl ether
  8. dry with materialThe organic phase is dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness in vacuo
  11. customto yield an oil
  12. customThis material is evacuated further under high vacuum

Sources & evidence

ORD record
ord-61bc4a148b444152b7b05f9b0be2d896
Source dataset
uspto-grants-2008_09
Patent number
US07423037B2

Reaction notes

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