4-Chlorotoluene → 4-(p-Tolyl)morpholine

HRID 412759Notes

Reaction equation

HRID 412759 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.CC(C)([O-])C.[Na+]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 78104-ChlorotolueneHCID 8083MorpholineHCID 23676156Sodium t-butoxide

Product 1

HCID 7662554-(p-Tolyl)morpholineYield 98%

Procedure

According to the general procedure B, 4-methylchlorobenzene (71 mg, 0.56 mmol) reacted with morpholine (46 mg, 0.53 mmol) using 1 mol % of catalyst and sodium tert-butoxide (60 mg, 1.03 mmol) at 70° C. for 27 h to give the title compound (92 mg, 98%) as a solid: 1H-NMR (300 MHz, CDCl3): δ 7.12 (d, 2H, J=8.7 Hz), 6.87 (d, 2H, J=8.7 Hz), 3.89 (t, 4H, J=4.8 Hz), 3.14 (t, 4H, J=4.8 Hz), 2.31 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 149.09, 129.64, 129.51, 115.97, 66.90, 49.86, 20.38. GC/MS(EI): m/z 177 (M+).

Workup

  1. customat 70° C.
  2. customfor 27 h

Sources & evidence

ORD record
ord-de6b4b60b6964a3f912e6b4bc9f1f06c
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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