1,1'-(Bromomethylene)bis(4-fluorobenzene) → 2-[4-[3-[Bis(4-fluorophenyl)methoxy]propyl]-1-piperazinyl]-6-chloropyrazine

HRID 35370Notes

Reaction equation

HRID 35370 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH:14](O)[CH2:15][CH3:16])[CH2:10][CH2:9]2)[CH:5]=[N:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25](Br)[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1.C(=O)(O)[O-:35].[Na+]>CN(C)C=O>[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[O:35][CH2:16][CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6]3[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[N:7]=3)[CH2:9][CH2:10]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 676651,1'-(Bromomethylene)bis(4-fluorobenzene)HCID 516892Sodium BicarbonateHCID 867423781-(6-Chloro-2-pyrazinyl)-4-piperazinyl propanol

Product 1

HCID 142339552-[4-[3-[Bis(4-fluorophenyl)methoxy]propyl]-1-piperazinyl]-6-chloropyrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(6-chloro-2-pyrazinyl)-4-piperazinyl propanol 3 g. (0.013 mol) in 50 ml. of dimethylformamide was added 3.3 g. (0.017 mol) of bis(4-fluorophenyl)methylbromide and 2.6 g. (0.034 mol) of sodium bicarbonate. The reaction mixture was refluxed overnight, dimethylformamide was evaporated under vacuum and the residue was extracted with methylene chloride (3×400 ml.). The methylene chloride extracts were collected, washed with water and dried (anhydrous Na2SO4). Evaporation of the methylene chloride afforded the title compound as a brown oil. HPLC purification afforded 2 g. (37% yield) of the pure product. It was converted to the (1:1) fumarate salt and recovered as the hemihydrate; m.p. 165°-167° C.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customdimethylformamide was evaporated under vacuum
  3. extractionthe residue was extracted with methylene chloride (3×400 ml.)
  4. customThe methylene chloride extracts were collected
  5. washwashed with water
  6. dry with materialdried (anhydrous Na2SO4)
  7. customEvaporation of the methylene chloride

Sources & evidence

ORD record
ord-aa5a0f291e6b415aaae345a373a5758e
Source dataset
uspto-grants-1988_08
Patent number
US04766215

Reaction notes

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