Diisopropylamine → HCID 7062386, compound

HRID 601030Notes

Reaction equation

HRID 601030 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][CH:12]1[O:17][CH:16]([CH3:18])[CH2:15][NH:14][CH2:13]1.C(NC(C)C)(C)C>O>[CH3:18][C@H:16]1[O:17][C@H:12]([CH3:11])[CH2:13][N:14]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15]1.[CH3:18][C@H:16]1[O:17][C@@H:12]([CH3:11])[CH2:13][N:14]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15]1

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 9590p-FluoronitrobenzeneHCID 1108622,6-Dimethylmorpholine

Product 2

HCID 7062386HCID 7062386, compoundHCID 7062388HCID 7062388, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-fluoro-4-nitrobenzene, 2,6-dimethylmorpholine (Purchased from Aldrich) and diisopropylamine was heated at 110° C. for 16 h. After being cooled to room temperature, the mixture was added water and extracted with EtOAc. The organic phase was dried over MgSO4, concentrated. The residue was purified by silica gel column chromatograghy eluted with EtOAc:hexanes (5 to 35% EtOAc) to give trans-2,6-dimethyl-4-(4-nitro-phenyl)-morpholine (258 mg) and cis-2,6-dimethyl-4-(4-nitro-phenyl)-morpholine (838 mg) both as yellow solids. Trans-isomer: MS (ES+): m/z=237.2; 1H NMR (CDCl3, 500 MHz): δ 1.30 (d, 6H), 3.17 (dd, 2H), 3.46 (dd, 2H), 4.15-4.22 (m, 2H), 6.77 (d, 2H), 8.14 (d, 2H). Cis-isomer: MS (ES+): m/z=237.2; 1H NMR (CDCl3, 500 MHz): δ 1.29 (d, 6H), 2.62 (dd, 2H), 3.67 (dd, 2H), 3.73-3.81 (m, 2H), 6.84 (d, 2H), 8.14 (d, 2H).

Workup

  1. temperatureAfter being cooled to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatograghy
  6. washeluted with EtOAc

Sources & evidence

ORD record
ord-33634d71e8a64e9dbb04e40a52895991
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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