Water → HCID 9867135, compound

HRID 2306158Notes

Reaction equation

HRID 2306158 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][O:10][CH2:11][CH:12]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22])[CH2:13][NH2:14].[CH2:23]([Br:26])[CH:24]=[CH2:25].C([O-])([O-])=O.[K+].[K+].O>O1CCCC1>[BrH:26].[CH2:25]([NH:14][CH2:13][CH:12]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22])[CH2:11][O:10][CH2:9][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])[CH:24]=[CH2:23]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 9927982HCID 9927982, compound

Product 1

HCID 9867135HCID 9867135, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g (3.3 mmol) of 3-(2,6-difluorophenyl)methoxy-2-(2,6-dimethylphenyl)-propylamine are dissolved in 10 ml of tetrahydrofuran (THF) and stirred with 0.4 g (3.3 mmol) of allylbromide and 1.2 g of K2CO3 for 16 h at ambient temperature. Then the solvent is eliminated in vacuo, the residue is combined with 50 ml of water and extracted twice with 30 ml of ethyl acetate. The organic phase is dried, concentrated by evaporation in vacuo and the residue is chromatographed on silica gel (methanol/dichloromethane=2:98). The appropriate fractions are concentrated by evaporation, the residue is dissolved in ether and the hydrobromide is precipitated with HBr/glacial acetic acid. Yield: 1.0 g (71%), melting point: 105° C.

Workup

  1. extractionextracted twice with 30 ml of ethyl acetate
  2. customThe organic phase is dried
  3. concentrationconcentrated by evaporation in vacuo
  4. customthe residue is chromatographed on silica gel (methanol/dichloromethane=2:98)
  5. concentrationThe appropriate fractions are concentrated by evaporation
  6. dissolutionthe residue is dissolved in ether
  7. customthe hydrobromide is precipitated with HBr/glacial acetic acid

Sources & evidence

ORD record
ord-4d1972e4c65d4897ad16ea8a728d9891
Source dataset
uspto-grants-2002_08
Patent number
US06441237B1

Reaction notes

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