Morpholine → 4-[5-(1,1-Dimethoxyethyl)-2-methoxy-3-trifluoromethylphenyl]morpholine

HRID 249725

Reaction equation

HRID 249725 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]([F:17])([F:16])[F:15])[C:3]=1[O:18][CH3:19].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[NH:66]1[CH2:71][CH2:70][O:69][CH2:68][CH2:67]1>>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[C:4]([C:14]([F:17])([F:16])[F:15])[C:3]([O:18][CH3:19])=[C:2]([N:66]2[CH2:71][CH2:70][O:69][CH2:68][CH2:67]2)[CH:7]=1)([O:12][CH3:13])[CH3:9]

Participants

4

Reactant 3

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 580856971-Bromo-5-(1,1-dimethoxyethyl)-2-methoxy-3-trifluoromethylbenzene

Product 1

HCID 580856994-[5-(1,1-Dimethoxyethyl)-2-methoxy-3-trifluoromethylphenyl]morpholine

Procedure

1-Bromo-5-(1,1-dimethoxyethyl)-2-methoxy-3-trifluoromethylbenzene (2 g) was initially introduced and argon was passed through with stirring for 0.5 h. Subsequently, the mixture was treated with Pd(II) acetate (13 mg), BINAP (54 mg) and sodium tertiary-butylate (784 mg), followed by morpholine (0.6 ml). The mixture obtained was stirred under argon at 85° C. for 8 h and after standing overnight at RT it was stirred at 85° C. for a further 8 h and allowed to stand overnight. The solvent was then stripped off and the residue was purified on silica gel (n-heptane-ethyl acetate gradient). 468 mg of the desired product were obtained.

Workup

  1. customThe mixture obtained
  2. stirringwas stirred under argon at 85° C. for 8 h
  3. waitafter standing overnight at RT
  4. stirringit was stirred at 85° C. for a further 8 h
  5. waitto stand overnight
  6. customthe residue was purified on silica gel (n-heptane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-60483acf475248b1b8834088ccafcae2
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Linked notes

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