Benzene, (2-bromoethoxy)- → HCID 178430563, compound

HRID 353110Notes

Reaction equation

HRID 353110 reaction equation
[CH3:1][CH:2]1[C:7]([CH3:19])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[N:16][NH:17][CH:18]=3)[CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3]1.Br[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:1][CH:2]1[C:7]([CH3:19])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[N:16][NH:17][CH:18]=3)[CH:9]=2)[CH2:6][CH2:5][N:4]([CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 68526Benzene, (2-bromoethoxy)-HCID 516892Sodium Bicarbonate2×HCID 178430465HCID 178430465, compound

Product 1

HCID 178430563HCID 178430563, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine (Preparation 44, 50 mg, 0.20 mmol) in N,N-dimethylformamide (6 mL) was added commercially available 2-(bromoethoxy)benzene (43 mg, 0.22 mmol) and sodium hydrogencarbonate (48 mg, 0.56 mmol). The resultant mixture was heated to 80° C. and stirred overnight. The reaction mixture was cooled, poured onto saturated aqueous sodium hydrogencarbonate solution (100 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over MgSO4, filtered and concentrated in vacuo to give an off-white gum. The crude product was partially purified by chromatography on a 5 g silica Waters Sep-Pak3 eluting with dichloromethane and then 5% methanol in dichloromethane. The pure fractions were collected to give the title compound as a clear oil as a clear gum (10 mg, 13.6%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an off-white gum
  7. customThe crude product was partially purified by chromatography on a 5 g silica Waters Sep-Pak3
  8. washeluting with dichloromethane
  9. customThe pure fractions were collected

Sources & evidence

ORD record
ord-1e0e21f837dd469893b908d433d1dfae
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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