Chlorobenzene → 4-Phenylmorpholine

HRID 1297506Notes

Reaction equation

HRID 1297506 reaction equation
CC(C)([O-])C.[K+].Cl[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>COCCOC>[C:8]1([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 8083MorpholineHCID 23665647Potassium tert-butoxide

Product 1

HCID 623394-Phenylmorpholine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

In air, potassium tert-butoxide (127 mg, 1.10 mmol) and complex Ih (6.8 mg, 0.01 mmol, 1.0 mol %) as defined in Example 1 were weighed into a vial with a stir bar and the vial was capped with a septum. The atmosphere was replaced with inert gas (Ar) and 1 mL of dry DME added and stirred until all the solids had dissolved. Chlorobenzene (102 μL, 112.56 mg, 1.0 mmol) and morpholine (96 μL, 96 mg, 1.10 mmol) were then added in quick succession with rapid stirring. The septum was then replaced with a Teflon® lined cap under inert gas (Ar) and the vial heated at 50° C. for 1 hour. After this time the reaction mixture was cooled and partitioned between water and ether, the organic phase was dried (anhydrous MgSO4), filtered, and the solvent removed. The resultant residue was purified by flash chromatography eluting with 9:1 pentane:ether. N-Phenylmorpholine was obtained as a white solid 155 mg, 95% yield.

Workup

  1. customthe vial was capped with a septum
  2. additionadded
  3. dissolutionhad dissolved
  4. customlined cap under inert gas (Ar)
  5. temperatureAfter this time the reaction mixture was cooled
  6. custompartitioned between water and ether
  7. dry with materialthe organic phase was dried (anhydrous MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed
  10. customThe resultant residue was purified by flash chromatography
  11. washeluting with 9:1 pentane

Sources & evidence

ORD record
ord-6e18a45d5ba34ed4ab9ecf767da66f3c
Source dataset
uspto-grants-2007_07
Patent number
US07250510B2

Reaction notes

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