Morpholine → 4-[3-Tert-butyl-5-(1,1-dimethoxyethyl)-2-methoxyphenyl]morpholine

HRID 244336Notes

Reaction equation

HRID 244336 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([O:12][CH3:13])([O:10][CH3:11])[CH3:9])[CH:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=1[O:18][CH3:19].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.CC(C)([O-])C.[Na+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([C:4]1[C:3]([O:18][CH3:19])=[C:2]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:7]=[C:6]([C:8]([O:12][CH3:13])([O:10][CH3:11])[CH3:9])[CH:5]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 230937191-Bromo-3-tert-butyl-5-(1,1-dimethoxyethyl)-2-methoxybenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 230937244-[3-Tert-butyl-5-(1,1-dimethoxyethyl)-2-methoxyphenyl]morpholine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under a nitrogen atmosphere, 2-bromo-6-tert-butyl-4-(1,1-dimethoxyethyl)anisole (650 g, 1.962 mol), palladium acetate (4.4 g 19.6 mmol, 1 mol %) and (±)-BINAP (18.3 g, 29.4 mmol, 1.5 mol %) were dissolved in 1,2-dimethoxyethane (1.96 L) at room temperature. To the resultant solution, morpholine (205 g, 2.36 mol) and sodium tert-butoxide (264 g, 2.75 mol) were added.

Sources & evidence

ORD record
ord-078c0f8d44b34a13850b8f2050974ec8
Source dataset
uspto-grants-2014_02
Patent number
US08658620B2

Reaction notes

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