Morpholine → 4-(2,6-Difluoro-4-nitrophenyl)morpholine

HRID 1417944Notes

Reaction equation

HRID 1417944 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[F:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[C:19]([F:26])[CH:18]=1>C(#N)C>[F:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[C:19]([F:26])[C:18]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 752721,3-Difluoro-5-nitrobenzeneHCID 81531Diisopropylethylamine

Product 1

HCID 223856304-(2,6-Difluoro-4-nitrophenyl)morpholineYield 47.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1.468 g of morpholine and 3.0 mL of diisopropylethylamine in 80 mL of acetonitrile was added a solution of 5.019 g of 2,6-difluoro-4-nitrobenzene (trifluoromethane) sulfonate in 10 mL of acetonitrile. The mixture was heated to reflux for 5 hours, then cooled and concentrated in vacuo. The residue was purified on a silica gel column (3 cm tall, 10 cm diam), eluting with 25% ethyl acetate/hexanes (v/v) and then 2% acetic acid/25% ethyl acetate/hexanes to give 1.95 g of an orange oil. This was washed with 5% ethyl acetate/hexanes, and the bright yellow solids air dried, mp 91°-920° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a silica gel column (3 cm tall, 10 cm diam)
  6. washeluting with 25% ethyl acetate/hexanes (v/v)

Sources & evidence

ORD record
ord-3950f11423614d56946be3bddb194241
Source dataset
uspto-grants-1999_03
Patent number
US05880118

Reaction notes

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