Morpholine → 4-Morpholinobenzonitrile

HRID 1296981Notes

Reaction equation

HRID 1296981 reaction equation
CC([O-])(C)C.[Na+].Cl[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:9][CH:10]=1)#[N:13]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 121634-ChlorobenzonitrileHCID 23676156Sodium t-butoxide

Product 1

HCID 3948084-MorpholinobenzonitrileYield 96.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

An oven-dried resealable Schlenk tube was purged with argon and charged with Pd2(dba)3 (11.5 mg, 0.025 mmol, 5 mol % Pd), 2 [Example 1] (14.8 mg, 0.075 mmol, 7.5 mol %), NaOt-Bu (68 mg, 0.71 mmol) and 4-chlorobenzonitrile (69 mg, 0.50 mmol). The tube was purged with argon then DME (0.5 mL) and morpholine (53 μL, 0.61 mmol) were added through a rubber septum. The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at room temperature for 26 h. The reaction was then diluted with EtOAc (20 mL), filtered through celite and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 91 mg (96%) of a tan solid.

Workup

  1. customAn oven-dried resealable Schlenk tube was purged with argon
  2. customThe tube was purged with argon
  3. customThe septum was removed
  4. customthe tube was sealed with a teflon
  5. customscrew cap
  6. additionThe reaction was then diluted with EtOAc (20 mL)
  7. filtrationfiltered through celite and
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c66bb401062d43138cf5eea2b07fe1be
Source dataset
uspto-grants-2007_07
Patent number
US07247731B2

Reaction notes

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