Sodium Bicarbonate → HCID 68193766, compound

HRID 920550Notes

Reaction equation

HRID 920550 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=1[N:34]=[C:35]=[O:36].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][O:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:35]([NH:34][C:28]3[C:29]([Cl:33])=[CH:30][CH:31]=[CH:32][C:27]=3[Cl:26])=[O:36])=[CH:16][CH:15]=2)[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholineHCID 178418339Butyllithium

Product 1

HCID 68193766HCID 68193766, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-benzyl-6-(4-bromo-phenyl)-morpholine (1.01 g; 3.04 mmol) in THF (25 mL) was added dropwise n-BuLi (1.2 mL; 2.5 mol/l in hexanes; 3.04 mmol), at −78° C. After 1 hour at −78° C., a solution of 2,6-dichlorophenyl isocyanate (0.63 g; 3.34 mmol) in THF (5 mL) was added dropwise. The mixture was allowed to warm to RT and then 5% aqueous NaHCO3 was added. Subsequently, the mixture was extracted with Et2O. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (Et2O:hexanes 1:1) to afford 4-(4-benzyl-morpholin-2-yl)-N-(2,6-dichloro-phenyl)-benzamide (0.68 g).

Workup

  1. customat −78° C
  2. extractionSubsequently, the mixture was extracted with Et2O
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (Et2O:hexanes 1:1)

Sources & evidence

ORD record
ord-a7542e44f747415f8ff70a33a889dff9
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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