Morpholine → 4-Morpholinobenzonitrile
Reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+].C1(C(C2C=CC=CC=2)=C(P(C2CCCCC2)C2CCCCC2)C)C=CC=CC=1.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:3][CH:4]=1)#[N:7]Participants
Conditions
- Temperature
- 100 °C
Procedure
Into a reactor were introduced 0.275 g (2.00 mmol) of 4-chlorobenzonitrile and 4 mL of toluene under a nitrogen atmosphere. The nitrile was dissolved in the solvent. To this solution were added 0.192 g (2.2 mmol) of morpholine, 0.231 g (2.4 mmol) of sodium t-butoxide, 4.5 mg (1 mol % based on the amine) of palladium acetate, and 15.6 mg (2 mmol % based on the amine) of the 1,1-diphenyl-2(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 14 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.304 g (81%) of N-(4-cyanophenyl)morpholine as light-yellow crystals. The results obtained are shown in Table 20.
Workup
- customThe resultant reaction mixture
- temperaturecooled
- extractionthis mixture was extracted with toluene
- dry with materialThe extract was dried with anhydrous magnesium sulfate
- customThereafter, the solvent was removed under reduced pressure
- customThe concentrate was purified by column chromatography
Sources & evidence
- ORD record
- ord-16f433635de14a6bbf2f73c864ef482c
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455720B1
Reaction notes
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