Morpholine → HCID 11106869, compound

HRID 412758Notes

Reaction equation

HRID 412758 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CC(C)([O-])C.[Na+]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8083MorpholineHCID 775951-Bromo-4-tert-butylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 11106869HCID 11106869, compoundYield 82%

Procedure

According to the general procedure B, 4-tert-butylbromobenzene (94 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 (72 mg, 82%) as a white solid: 1H-NMR (300 MHz, CDCl3): δ 7.35 (d, 2H, J=8.7 Hz), 6.91 (d, 2H, J=8.7 Hz), 3.89 (t, 4H, J=4.5 and 4.8 Hz), 3.17 (t, 4H, J=4.5 and 4.8 Hz), 1.34 (s, 9H). 13C{1H}-NMR (100 MHz, CDCl3): δ 148.89, 142.76, 125.95, 115.38, 66.99, 49.54, 33.94, 31.42. GC/MS(EI): m/z 219 (M+), 204 (M+−CH3), 146 (M+−morpholine).

Workup

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

Sources & evidence

ORD record
ord-e2388b567ef8482286adc89c52ab2bb8
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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