Morpholine → 4-(3-Methoxyphenyl)morpholine

HRID 412757

Reaction equation

HRID 412757 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+]>>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 169713-BromoanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 99643354-(3-Methoxyphenyl)morpholineYield 96%

Procedure

According to the general procedure B, 3-bromoanisole (82 mg, 0.44 mmol) reacted with morpholine (36 mg, 0.41 mmol) using 1 mol % of catalyst and sodium tert-butoxide (42 mg, 0.44 mmol) at 100° C. for 21 h to give the title compound (76 mg, 96%) as an oil: 1H-NMR (300 MHz, CDCl3): δ 7.21 (t, 1H, J=8.1 and 8.7 Hz), 6.57-6.45 (m, 3H), 3.87 (t, 4H, J=4.5 and 5.1 Hz), 3.81 (s, 3H), 3.17 (t, 4H, J=4.5 and 5.1 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 160.00, 152.67, 129.83, 108.43, 104.68, 102.18, 66.86, 55.15, 49.25. GC/MS(EI): m/z 193 (M+).

Workup

  1. customat 100° C.
  2. customfor 21 h

Sources & evidence

ORD record
ord-b16ab7a107794e0284667a499c88a514
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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