Water → HCID 14553817, compound

HRID 1904283Notes

Reaction equation

HRID 1904283 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH2:10][CH:11]([CH3:21])[CH2:12][N:13]2[CH2:18][CH:17]([CH3:19])[O:16][CH:15]([CH3:20])[CH2:14]2)[CH:7]=[CH:8][CH:9]=1.I[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.O>CN(C)C=O>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([O:3][C:4]2[CH:5]=[C:6]([CH2:10][CH:11]([CH3:21])[CH2:12][N:13]3[CH2:14][CH:15]([CH3:20])[O:16][CH:17]([CH3:19])[CH2:18]3)[CH:7]=[CH:8][CH:9]=2)=[CH:24][CH:25]=1)([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 124951-Iodo-4-nitrobenzeneHCID 24758Sodium hydrideHCID 1787113-(3-(2,6-Dimethylmorpholin-4-yl)-2-methylpropyl)phenol

Product 1

HCID 14553817HCID 14553817, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Dimethylformamide (5 ml) was added to 60% sodium hydride (0.12 g) under nitrogen stream, and a solution of 4-[3-(3-hydroxyphenyl)-2-methylpropyl]-2,6-dimethylmorpholine (0.48 g) in dimethylformamide (5 ml) was added thereto in 30 minutes, followed by stirring at room temperature for 2 hours. To the reaction mixture, p-iodonitrobenzene (0.97 g) and cuprous chloride (0.1 g) were added, and the resultant mixture was heated under reflux for 10 hours. Then, water (100 ml) was added to the reaction mixture, which was filtered through celite. The celite was washed with toluene (200 ml). The toluene layer and the toluene washing were combined together and shaken with 15% aqueous sodium hydroxide solution (30 ml). The toluene layer was separated, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to give 4-[3-(3-(4-nitrophenoxy)phenyl)-2-methylpropyl]-2,6-dimethylmorpholine (cis-isomer, 0.27 g).

Workup

  1. temperatureunder reflux for 10 hours
  2. filtrationwas filtered through celite
  3. washThe celite was washed with toluene (200 ml)
  4. stirringshaken with 15% aqueous sodium hydroxide solution (30 ml)
  5. customThe toluene layer was separated
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-aa431b8fee444548ab8af281849d8caf
Source dataset
uspto-grants-1989_06
Patent number
US04837236

Reaction notes

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