Sodium → [2-(2-Benzyloxy-ethoxy)-5-methoxy-benzyl]-(5-fluoro-2-phenoxy-phenyl)-amine

HRID 1717511Notes

Reaction equation

HRID 1717511 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH2:8])[CH:7]=1.[CH2:16]([O:23][CH2:24][CH2:25][O:26][C:27]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:28]=1[CH:29]=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na]>ClC(Cl)C.O>[CH2:16]([O:23][CH2:24][CH2:25][O:26][C:27]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:28]=1[CH2:29][NH:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 5360545SodiumHCID 196271325-Fluoro-2-phenoxyanilineHCID 86189517HCID 86189517, compound

Product 1

HCID 67104233[2-(2-Benzyloxy-ethoxy)-5-methoxy-benzyl]-(5-fluoro-2-phenoxy-phenyl)-amineYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To stirred solution of 4.6 g (23 mmol) 1b, 6.3 g (23 mmol) 2a and one drop of glacial acid in 35 ml dichloroethane (pH=5) were added 7.4 g (35 mmol) sodium tris-acetoxy hydro borane. The reaction mixture was stirred over night and diluted with 3 ml water. The pH value was adjusted with aqueous sodium hydroxyd solution to pH=8-9. The mixture was extracted three times with dichloromethane. The combined organic phases were washed with water and brine and were dried with magnesium sulfate. The desired crude product 2b was obtained in 78% yield (8.5 g, 17.9 mmol) as yellow oil. The crude product 2b was used without further purification.

Workup

  1. extractionThe mixture was extracted three times with dichloromethane
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialwere dried with magnesium sulfate

Sources & evidence

ORD record
ord-a33aec81925643d49a17171ce650357a
Source dataset
uspto-grants-2010_09
Patent number
US07803960B2

Reaction notes

Loading…