Diethyl Ether → HCID 66594865, compound

HRID 1091363Notes

Reaction equation

HRID 1091363 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([C:14]2[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cu](C#N)[C:24]#[N:25].C(OCC)C.[OH-].[Na+]>CN1CCCC1=O>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([C:14]2[CH:19]=[C:18]([C:24]#[N:25])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 66594849HCID 66594849, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 66594865HCID 66594865, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of (2S)-4-benzyl-2-(5-bromo-2-methoxyphenyl)-morpholine (17.1 g, 47.2 mmol) and copper cyanide (6.35 g, 70.9 mmol) in 1-methyl-2-pyrrolidinone (140 ml) was stirred at 160° C. for 9 hours. Diethyl ether and 1N aqueous sodium hydroxide were added to the reaction mixture, and the solution was passed through Celite column. The whole was extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give (2S)-4-benzyl-2-(5-cyano-2-methoxyphenyl)-morpholine (10.1 mg, 69%) as a yellow oil.

Workup

  1. extractionThe whole was extracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8578adf83599446790ebf50d43141f24
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

Loading…