Morpholine → 4-Morpholinobenzonitrile

HRID 412760Notes

Reaction equation

HRID 412760 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+]>>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:3][CH:4]=1)#[N:9]

Participants

4

Reactant 3

HCID 8083MorpholineHCID 121634-ChlorobenzonitrileHCID 23676156Sodium t-butoxide

Product 1

HCID 3948084-MorpholinobenzonitrileYield 82%

Procedure

According to the general to procedure B, 4-chlorocyanobenzene (71 mg, 0.52 mmol) reacted with morpholine (53 mg, 0.61 mmol) using 1 mol % of catalyst and sodium tert-butoxide (58 mg, 0.60 mmol) at 45° C. for 27 h to give the title compound (77 mg, 82%) as a solid: 1H-NMR (400 MHz, CDCl3): δ 7.49 (d, 2H, J=8.0 Hz), 6.85 (d, 2H, J=8.8 Hz), 3.84 (t, 4H, J=4.8 Hz), 3.27 (t, 4H, J=4.8 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 153.36, 133.36, 119.76, 113.93, 100.69, 66.31, 47.15. GC/MS(EI): m/z 188 (M+).

Workup

  1. customat 45° C.
  2. customfor 27 h

Sources & evidence

ORD record
ord-b69e61825d6e4f53a813f36b6efdf245
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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