Sodium hydride → 4-Benzyl-2-{4-[2-(2,6-dichloro-phenyl)-vinyl]-phenyl}-morpholine

HRID 920551Notes

Reaction equation

HRID 920551 reaction equation
[Br-].[Cl:2][C:3]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].[CH2:32]([N:39]1[CH2:44][CH2:43][O:42][CH:41]([C:45]2[CH:52]=[CH:51][C:48]([CH:49]=O)=[CH:47][CH:46]=2)[CH2:40]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:32]([N:39]1[CH2:44][CH2:43][O:42][CH:41]([C:45]2[CH:46]=[CH:47][C:48]([CH:49]=[CH:5][C:4]3[C:25]([Cl:29])=[CH:26][CH:27]=[CH:28][C:3]=3[Cl:2])=[CH:51][CH:52]=2)[CH2:40]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 118435512,6-Dichlorobenzyltriphenylphosphonium bromideHCID 866700124-(4-Benzyl-morpholin-2-yl)-benzaldehyde

Product 1

HCID 670323004-Benzyl-2-{4-[2-(2,6-dichloro-phenyl)-vinyl]-phenyl}-morpholineYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (2,6-dichloro-benzyl)-triphenyl-phosphonium bromide (2.06 g; 4.1 mmol) (See: A. Schmidpeter, H. Noeth, G. Jochem, H.-P. Schroedel, K. Karaghiosoff; Chem. Ber., 1995, 128, 379) in THF (25 mL) was added sodium hydride (60% dispersion in mineral oil) (215 mg; 4.5 mmol), at 0° C. After stirring for 1 hour, 4-(4-benzyl-morpholin-2-yl)-benzaldehyde (1.05 g; 3.7 mmol) was added, at 0° C. Subsequently, the resulting mixture was heated under reflux for 1 hour. After cooling to RT, 5% aqueous NaHCO3 was added and the mixture extracted with Et2O. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford 4-benzyl-2-{4-[2-(2,6-dichloro-phenyl)-vinyl]-phenyl}-morpholine (1.15 g).

Workup

  1. customat 0° C
  2. temperatureSubsequently, the resulting mixture was heated
  3. temperatureunder reflux for 1 hour
  4. extractionthe mixture extracted with Et2O
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1)

Sources & evidence

ORD record
ord-61ffdcd65a1d44cca35b7631a1f2007e
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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